2014

Organic
Chemistry
Comprehensive Tutorial notes
Incorporating Hydrocarbons ,alkanols,
alkanoic acids, detergents ,polymers and
fibres

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Introduction to Organic chemistry .
Organic chemistry is the branch of chemistry
that studies carbon compounds present in living
things, once living things or synthetic/man-made.
Compounds that makes up living things whether
alive or dead mainly contain carbon.
Carbon is tetravalent. It is able to form stable
covalent bonds with itself and many non-metals
like Hydrogen, Nitrogen ,Oxygen and halogens to
form a variety of compounds.
This is because:
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(i).Carbon uses all the four valence electrons to form four
strong covalent bond.
(ii).Carbon can covalently bond to form a single, double
or triple covalent bond with itself.
(iii).Carbon atoms can covalently bond to form a very long
chain or ring.
When carbon covalently bond with Hydrogen, it forms a
group of organic compounds called Hydrocarbons.
HYDROCARBONS.
Hydrocarbons are a group of organic compounds
containing /made up of hydrogen and carbon atoms only.
Depending on the type of bond that exist between the
individual carbon atoms, hydrocarbons are classified as:
(i). Alkanes (ii). Alkenes (iii). Alkynes!
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(i) Alkanes.

(a)Nomenclature/Naming
These are hydrocarbons with a general
formula CnH2n+2 where n is the number of
Carbon atoms in a molecule.
The carbon atoms are linked by single bond
to each other and to hydrogen atoms.
They include:
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n General/Molecula Structural formula Name
formula
1 CH4 H Methane
H C H
H
2 C2H6 H H Ethane
H C C H
H H
CH2CH2
3 C3H8 H H H Propane
H C C C H
H H H
CH2CH2 CH3
4 C4H10 H H H H Butane
H C C C C H
H H H H
CH3 (CH2) 2CH3
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5 C5H12 H H H H H Pentane

H C C C C C H

H H H H H
CH3 (CH2) 3 CH3

6 C6H14 H H H H H H Hexane

H C C C C C C H

H H H H H H
CH3 (CH2) 4 CH3
7 C7H16 H H H H H H H Heptane

H C C C C C C C H

H H H H H H H
CH3 (CH2) 5 CH3

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8 C8H18 H H H H H H H H Octane

H C C C C C C C C H

H H H H H H H H
CH3 (CH2) 6CH3

9 C9H20 H H H H H H H H H Nonane

H C C C C C C C C C H

H H H H H H H H H
CH3 (CH2) 7 CH3
10 C10H22 H H H H H H H H H H decane

H - C- C C C C C C C C C H

H H H H H H H H H H
CH3 (CH2) 8CH3

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Note
1.The molecular formular of a compound is the number
of each atoms of elements making the compound e.g.
Decane has a general/molecular formula C10H22 ;this
means there are 10 carbon atoms and 22 hydrogen atoms
in a molecule of decane.
2.The structural formula is the arrangement / bonding of
atoms of each element making the compound e.g
Decane has the structural formula as in the table
above ;this means the 1st carbon from left to right is
bonded to three hydrogen atoms and one carbon atom.
The 2nd carbon atom is joined/bonded to two other carbon
atoms and two Hydrogen atoms. e.t.c.
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3.Since carbon is tetravalent ,each atom of carbon in the
alkane MUST always be bonded using four covalent
bond /four shared pairs of electrons.
4.Since Hydrogen is monovalent ,each atom of
hydrogen in the alkane MUST always be bonded using
one covalent bond/one shared pair of electrons.
5.One member of the alkane differ from the
next/previous by a -CH2 - group.
e.g
Propane differ from ethane by one Carbon and two
Hydrogen atoms form ethane. Ethane differ from
methane also by one carbon and two Hydrogen atoms.
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6.A group of compounds that differ by a -CH2 - group
from the next /previous consecutively is called a
homologous series.
7.A homologous series:
(i) differ by a CH2 group from the next /previous
consecutively
(ii)have similar chemical properties
(iii)have similar chemical formula that can be
represented by a general formula e.g
alkanes have the general formula CnH2n+2.
(iv)the physical properties (e.g.melting/boiling
points)show steady gradual change)
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 8.The 1st four alkanes have the prefix meth_,eth_,prop_
and but_ to represent 1,2,3 and 4 carbons in the
compound. All other use the numeral prefix
pent_,Hex_,hept_ , etc to show also the number of
carbon atoms.
9.If one hydrogen atom in an alkane is removed, an alkyl
group is formed.e.g
Alkane molecular Alkyl Molecula structure
name structure name
CnH2n+2 CnH2n+1
methane CH4 methyl CH3
ethane CH3CH3 ethyl CH3 CH2
propane CH3 CH2 CH3 propyl CH3 CH2 CH2
butane CH3CH2CH2 CH3 butyl CH3 CH2 CH2 CH2
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(b)Isomers of alkanes
Isomers are compounds with the same molecular formula
but different structural formula.
Isomerism is the existence of a compounds having the
same molecular formula but different structural formula.
The 1st three alkanes do not form isomers.Isomers are
named by using the IUPAC(International Union of Pure
and Applied Chemistry) system of nomenclature
/naming.
The IUPAC system of nomenclature uses the following
basic rules/guidelines:
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1.Identify the longest continuous carbon chain to
get/determine the parent alkane.
2.Number the longest chain form the end of the chain
that is near the branches so as the branch get the lowest
number possible
3. Determine the position, number and type of branches.
Name them as methyl, ethyl, propyl e.tc. according to
the number of carbon chains attached to the parent
alkane.
Name them fluoro-,chloro-,bromo-,iodo- if they are
halogen
4.Use prefix di-,tri-,tetra-,penta-,hexa- to show the
number of branches attached to the parent alkane.
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 Practice on IUPAC nomenclature of alkanes
(a)Draw the structure of:
(i)2-methylbutane
Procedure
1. Identify the longest continuous carbon chain to
get/determine the parent alkane.
Butane is the parent name CH3 CH2 CH2 CH3

2. Number the longest chain form the end of the chain

that is near the branches so as the branch get the lowest
number possible
The methyl group is attached to Carbon “2”

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3. Determine the position, number and type of branches.

Name them as methyl, ethyl, propyl e.tc. according to the

number of carbon chains attached to the parent alkane i.e

Position of the branch at carbon “2”

Number of branches at carbon “1”
Type of the branch “methyl” hence

Molecular formula
CH3

CH3 CH CH2 CH3 // CH3 CH (CH3 ) CH2CH3

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Structural formula

H H H H

H C C C C H

H H H

H C H

H
(ii)2,2-dimethylbutane
Procedure [email protected] 16
1. Identify the longest continuous carbon chain to
get/determine the parent alkane.
Butane is the parent name CH3 CH2 CH2 CH3

2. Number the longest chain form the end of the chain that
is near the branches so as the branch get the lowest
number possible
The methyl group is attached to Carbon “2”
3. Determine the position, number and type of branches.
Name them as methyl, ethyl, propyl e.tc. according to the
number of carbon chains attached to the parent alkane i.e
Position of the branch at carbon “2”
Number of branches at carbon “2”
Type of the branch two“methyl” hence
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Molecular formular
CH3

CH3 C CH2 CH3 // CH3 C (CH3 )2 CH2CH3

CH3 H
Structural formula H C H
H H H

H C C C C H

H H H
H C H
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H
(iii) 2,2,3-trimethylbutane
Procedure
1. Identify the longest continuous carbon chain to get/determine
the parent alkane.
Butane is the parent name CH3 CH2 CH2 CH3
2. Number the longest chain form the end of the chain that is near
the branches so as the branch get the lowest number possible
The methyl group is attached to Carbon “2 and 3”
3. Determine the position, number and type of branches.
Name them as methyl, ethyl, propyl e.tc. according to the number
of carbon chains attached to the parent alkane i.e
Position of the branch at carbon “2 and 3”
Number of branches at carbon “3”
Type of the branch three “methyl” hence
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 CH3

CH3 C CH CH3 // CH3 C (CH3 )3 CH2CH3

CH3 CH3
Structural formula H H

H C H H C H
H H

H C C C C H
H H H
H C H [email protected] 20

H
(ii) 1,1,1-tetrachloro-2,2-dimethyl-butane
CH3

CCl 3 C CH3 // C Cl 3 C (CH3 )2 CH3

CH3

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(ii) 1,1,1-tetrachloro-2,2-dimethyl-butane
Molecular formular
CH3

CCl3 C CH3 // CCl3 C (CH3 )2 CH3

CH3 H
Structural formula H C H
Cl H H
Cl C C C C H
Cl H H
H C H
H
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(c)Occurrence and extraction
Crude oil ,natural gas and biogas are the main sources
of alkanes:
(i)Natural gas is found on top of crude oil deposits and
consists mainly of methane.
(ii)Biogas is formed from the decay of waste organic
products like animal dung and cellulose.
When the decay takes place in absence of oxygen , 60-
75% by volume of the gaseous mixture of methane gas is
produced.
(iii)Crude oil is a mixture of many flammable
hydrocarbons/substances.
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Using fractional distillation, each hydrocarbon fraction
can be separated from the other.

The hydrocarbon with lower /smaller number of carbon

atoms in the chain have lower boiling point and thus
collected first.
As the carbon chain increase, the boiling point,
viscosity (ease of flow) and colour intensity increase as
flammability decrease.
Hydrocarbons in crude oil are not pure.
They thus have no sharp fixed boiling point.

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Carbon atoms in Common name of Uses of fraction
a molecule fraction
1-4 Gas L.P.G gas for domestic
use
5-12 Petrol Fuel for petrol engines
9-16 Kerosene/Paraffin Jet fuel and domestic
lighting/cooking

15-18 Light diesel Heavy diesel engine fuel

18-25 Diesel oil Light diesel engine fuel

20-70 Lubricating oil Lubricating oil to reduce

friction.
Over 70 Bitumen/Asphalt Tarmacking roads
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(d)School laboratory preparation of alkanes
In a school laboratory, alkanes may be prepared from the
reaction of a sodium alkanoate with solid sodium
hydroxide /soda lime.
Chemical equation:
Sodium alkanoate+soda lime -> alkane +Sodium carbonate
CnH2n+1COONa(s) +NaOH(s) -> C n H2n+2 + Na2CO3(s)
The “H” in NaOH is transferred/moves to the CnH2n+1 in
CnH2n+1COONa(s) to form C n H2n+2.
Examples
1. Methane is prepared from the heating of a mixture of
sodium ethanoate and soda lime and collecting over water
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Sodium ethanoate + soda lime->
methane + Sodium carbonate
CH3COONa(s) +NaOH(s) ->C H4 + Na2CO3(s)
The “H” in NaOH is transferred/moves to the CH3 in
CH3COONa(s) to form CH4.
2. Ethane is prepared from the heating of a mixture of
sodium propanoate and soda lime and collecting over
water
Sodium propanoate + soda lime->
ethane+Sodium carbonate
CH3 CH2COONa(s) +NaOH(s)->CH3 CH3 +Na2CO3(s)
The “H” in NaOH is transferred/moves to the CH3 CH2 in
CH3 CH2COONa (s) to form CH3 CH3
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3. Propane is prepared from the heating of a mixture of sodium
butanoate and soda lime and collecting over water
Sodium butanoate+soda lime->propane +Sodium carbonate
CH3 CH2CH2COONa(s) +NaOH(s) -> CH3 CH2CH3 + Na2CO3(s)
The “H” in NaOH is transferred/moves to the CH3 CH2CH2 in CH3
CH2CH2COONa to form CH3 CH2CH3

4. Butane is prepared from the heating of a mixture of sodium

pentanoate and soda lime and collecting over water
Sodium pentanoate + soda lime -> butane + Sodium carbonate
CH3 CH2 CH2CH2COONa(s)+NaOH(s) ->
CH3 CH2CH2CH3 + Na2CO3(s)
The “H” in NaOH is transferred/moves to the CH3CH2 CH2 CH2 in
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CH3 CH2CH2 CH2COONa (s) to form CH3 CH2 CH2CH3
Laboratory set up for the preparation of alkanes

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Properties of alkanes
Alkanes are colourless gases, solids and liquids that are
not poisonous.
They are slightly soluble in water.
The solubility decrease as the carbon chain increase.
The melting and boiling point increase as the carbon chain
increase.
This is because of the increase in van-der-waals /
intermolecular forces as the carbon chain increase.
The 1st four straight chain alkanes (methane, ethane,
propane and butane) are therefore gases
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The next six (pentane ,hexane, heptane,octane,nonane,
decane) are liquids.
From unidecane ,alkane with 11 carbon atoms are solids .

The density of straight chain alkanes increase with

increasing carbon chain as the intermolecular forces
increases.

This reduces the volume occupied by a given mass of the

compound.

Summary of physical properties of alkanes

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Alkane General Melting Boiling Density State at room(298K)
formula point(K) point(K) gcm-3 temperature and pressure
atmosphere (101300Pa)
Methane CH4 90 112 0.424 gas

Ethane CH3CH3 91 184 0.546 Gas

Propane CH3CH2CH3 105 231 0.501 gas

Butane CH3(CH2)2CH3 138 275 0.579 gas

Pentane CH3(CH2)3CH3 143 309 0.626 liquid

Hexane CH3(CH2)4CH3 178 342 0.657 liquid

Heptane CH3(CH2)5CH3 182 372 0.684 liquid

Octane CH3(CH2)6CH3 216 399 0.703 liquid

Nonane CH3(CH2)7CH3 219 424 0.708 liquid

Octane CH3(CH2)8CH3 243 447 0.730 liquid

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Chemical properties
(i)Burning.
Alkanes burn with a blue/non-luminous non-sooty/non-smoky
flame in excess air to form carbon(IV) oxide and water.
Alkane + Air -> carbon(IV) oxide +water (excess air/oxygen)
Alkanes burn with a blue/non-luminous non-sooty/non-smoky
flame in limited air to form carbon(II) oxide and water.
Alkane + Air -> carbon(II) oxide +water (limited air)
Examples
1.(a) Methane when ignited burns with a blue non sooty flame in
excess air to form carbon(IV) oxide and water.
Methane + Air -> carbon(IV) oxide +water (excess air/oxygen)
CH4(g) + 2O2(g)-> CO2(g) +2H2O(l/g)
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 (b) Methane when ignited burns with a blue non sooty flame in
limited air to form carbon(II) oxide and water.
Methane + Air -> carbon(II) oxide +water (excess air/oxygen)
2CH4(g)+ 3O2(g)-> 2CO(g) +4H2O(l/g)
2.(a) Ethane when ignited burns with a blue non sooty flame in
excess air to form carbon(IV) oxide and water.
Ethane + Air -> carbon(IV) oxide +water (excess air/oxygen)
2C2H6(g)+ 7O2(g)-> 4CO2(g) +6H2O(l/g)
(b) Ethane when ignited burns with a blue non sooty flame in
limited air to form carbon(II) oxide and water.
Ethane + Air -> carbon(II) oxide +water (excess air/oxygen)
2C2H6(g)+ 5O2(g)-> 4CO(g) +6H2O(l/g)
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3.(a) Propane when ignited burns with a blue non sooty flame in
excess air to form carbon(IV) oxide and water.
Propane + Air -> carbon(IV) oxide +water (excess air/oxygen)
C3H8(g)+ 5O2(g)-> 3CO2(g) +4H2O(l/g)
(b) Ethane when ignited burns with a blue non sooty flame in
limited air to form carbon(II) oxide and water.
Propane + Air -> carbon(II) oxide +water (excess air/oxygen)
2C3H8(g)+ 7O2(g)-> 6CO(g) +8H2O(l/g)
ii)Substitution
Substitution reaction is one in which a hydrogen atom is
replaced by a halogen in presence of ultraviolet light.
Alkanes react with halogens in presence of ultraviolet
light to form halogenoalkanes. [email protected] 35
During substitution:
(i)the halogen molecule is split into free atom/radicals.
(ii)one free halogen radical/atoms knock /remove one
hydrogen from the alkane leaving an alkyl radical.
(iii) the alkyl radical combine with the other free halogen
atom/radical to form halogenoalkane.
(iv)the chlorine atoms substitute repeatedly in the alkane.
Each substitution removes a hydrogen atom from the
alkane and form hydrogen halide.
(v)substitution stops when all the hydrogen in alkanes are
replaced with halogens.
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Substitution reaction is a highly explosive reaction in
presence of sunlight / ultraviolet light that act as catalyst.
Examples of substitution reactions
Methane has no effect on bromine or chlorine in diffused
light/dark.
In sunlight , a mixture of chlorine and methane explode to
form colourless mixture of chloromethane and hydrogen
chloride gas.
The pale green colour of chlorine gas fades.
Chemical equation
1.(a)Methane + chlorine ->
Chloromethane+Hydrogen chloride
CH4(g) + Cl2(g) -> CH3Cl (g) + HCl (g)
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 H H
H C H + Cl Cl -> H C Cl + H Cl
H H
chloromethane

H H

H C Cl + Cl Cl -> H C Cl + H Cl

H Cl
Dichloromethane
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 H Cl
H C Cl + Cl Cl -> H C Cl + H Cl
Cl Cl
trichloromethane

Cl Cl

H C Cl + Cl Cl -> Cl C Cl + H Cl

Cl Cl
tetrachloromethane
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Ethane has no effect on bromine or chlorine in
diffused light/dark.
In sunlight , a mixture of bromine and ethane
explode to form colourless mixture of
bromoethane and hydrogen chloride gas.
The red/brown colour of bromine gas fades.
Chemical equation
(a)Ethane + Bromine ->
bromoethane +Hydrogen chloride
CH3CH3(g)+ Br2(g)-> CH3CH2Br (g)+HBr (g)
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 H H H H

H C C H + Br Br -> H C C Br + H Br

H H H H
bromoethane

H H H H

H C C Br + Br Br -> H C C Br + H Br

H H H Br
1,1-dibromoethane

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 H H H Br

H C C Br + Br Br -> H C C Br + H Br

H Br H Br
1,1,1-tribromoethane

H Br H Br

H C C Br + Br Br -> H C C Br + H Br

Br Br Br Br
1,1,1,2-tetrabromoethane

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 H Br H Br

H C C Br +Br Br ->Br C C Br + H Br

Br Br Br Br
1,1,1,2,2-pentabromoethane

H Br Br Br

Br C C Br + Br Br -> Br C C Br + H Br

Br Br Br Br
1,1,1,2,2,2-hexabromoethane

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Uses of alkanes
1.Most alkanes are used as fuel e.g.
Methane is used as biogas in homes.
Butane is used as the Laboratory gas.
2.On cracking ,alkanes are a major source of
Hydrogen for the manufacture of ammonia/Haber
process.
3.In manufacture of Carbon black which is a
component in printers ink.
4.In manufacture of useful industrial chemicals like
methanol, methanol, and chloromethane.
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(ii) Alkenes
(a)Nomenclature/Naming

These are hydrocarbons with a general formula CnH2n

and C C double bond as the functional

group .
n is the number of Carbon atoms in the molecule.

The carbon atoms are linked by at least one double bond

to each other and single bonds to hydrogen atoms.

They include:
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n General/ Structural formula Name
Molecular
formula
1 Does not exist
2 C2H4 H H Ethene
H C C H
CH2 CH2
3 C3H6 H H H Propene
H C C C H
H
CH2 CH CH3
4 C4H8 H H H H Butene
H C C C C H
H H
CH2 CH CH2CH3
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5 C5H12 H H H H H Pentene
H C C C C C H
H H H
CH2 CH (CH2)2CH3
6 C6H14 H H H H H H Hexene
H C C C C C C H
H H H H
CH2 CH (CH2)3CH3
7 C7H16 H H H H H H H Heptene
H C C C C C C C H

H H H H H H H
CH2 CH (CH2)4CH3
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8 C8H18 H H H H H H H H Octene
H C C C C C C C C H
H H H H H H
CH2 CH (CH2)5CH3

9 C9H20 H H H H H H H H H Nonene
H C C C C C C C C C H
H H H H H H H
CH2 CH (CH2)6CH3

10 C10H22 H H H H H H H H H H decene
H C C C C C C C C C C H
H H H H H H H H
CH2 CH (CH2)7CH3

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Note
1.Since carbon is tetravalent ,each atom of carbon in the
alkene MUST always be bonded using four covalent
bond /four shared pairs of electrons including at the
double bond.
2.Since Hydrogen is monovalent ,each atom of
hydrogen in the alkene MUST always be bonded using
one covalent bond/one shared pair of electrons.
3.One member of the alkene ,like alkanes,differ from the
next/previous by a CH2 group.They also form a
homologous series.
e.g
Propene differ from ethene by one carbon and two
Hydrogen atoms from ethene. [email protected] 49
 4.A homologous series of alkenes like that of alkanes:
(i) differ by a CH2 group from the next /previous
(ii)have similar chemical properties
(iii)have similar chemical formula represented by
the general formula CnH2n
(iv)the physical properties show gradual change
5.The = C= C = double bond in alkene is the
functional group.
A functional group is the reacting site of a molecule
/compound.
6. The = C= C = double bond in alkene can easily be
broken to accommodate two more monovalent atoms.
The = C= C = double bond in alkenes make it thus
unsaturated. [email protected] 50
7. An unsaturated hydrocarbon is one with a
double =C=C= or triple – C C – carbon
bonds in their molecular structure.
Unsaturated hydrocarbon easily reacts to be
saturated.
8.A saturated hydrocarbon is one without a
double
=C=C= or triple – C C – carbon bonds in
their molecular structure.
Most of the reactions of alkenes take place at the
= C = C =bond. [email protected] 51
(b).Isomers of alkenes
Isomers of alkenes like alkanes have the same molecular
formula but different structural formula.
Isomers of alkenes are also named by using the
IUPAC(International Union of Pure and Applied
Chemistry) system of nomenclature/naming.
The IUPAC system of nomenclature of naming alkenes
uses the following basic rules/guidelines:
1.Identify the longest continuous/straight carbon chain
which contains the =C = C= double bond get/determine
the parent alkene.
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2.Number the longest chain form the end of the chain
which contains the =C = C= double bond so the =C =
C= double bond lowest number possible.
3 Indicate the positions by splitting “alk-positions-ene”
e.g. but-2-ene, pent-1,3-diene.
4.The position indicated must be for the carbon atom at
the lower position in the =C = C= double bond.i.e
But-2-ene means the double =C = C= is between
Carbon “2”and “3”
Pent-1,3-diene means there are two double bond one
between carbon “1” and “2”and another between carbon
“3” and “4”
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5. Determine the position, number and type of branches.
Name them as methyl, ethyl, propyl e.tc. according to the
number of alkyl carbon chains attached to the alkene.
Name them fluoro-,chloro-,bromo-,iodo- if they are
halogens

6.Use prefix di-,tri-,tetra-,penta-,hexa- to show the

number of double C = C bonds and branches attached
to the alkene.

7.Position isomers can be formed when the =C = C=

double bond is shifted between carbon atoms e.g.
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But-2-ene means the double =C = C= is between Carbon “2”and
“3”
But-1-ene means the double =C = C= is between Carbon “1”and
“2”
Both But-1-ene and But-2-ene are position isomers of Butene
8.Position isomers are molecules/compounds having the same
general formular but different position of the functional group. i.e.
Butene has the molecular/general formular C4H8 position but can
form both But-1-ene and But-2-ene as position isomers.
9. Like alkanes ,an alkyl group can be attached to the alkene.
Chain/branch isomers are thus formed.
10.Chain/branch isomers are molecules/compounds having the
same general formula but different structural formula . e.g
Butene and 2-methyl propene both have the same general formualr
but different branching chain. [email protected] 55
Practice on IUPAC nomenclature of alkenes
H H H H

H C C C C H But-1-ene(double bond is
between carbon “1-2”

H H

H H H H

H C C C C H But-2-ene(double bond is
between carbon “2-3”

H H [email protected] 56
 H CH3 H H

H C C C C H 2-methylbut-1-ene(double
bond is between carbon
H H “1-2” and methyl group at
carbon “2”
H CH3 CH3 H

H C C C C H 2,3-dimethylbut-2-ene
(double bond is between
H H carbon “2-3” and
two methyl group at carbon
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“2-3”
 H CH3 CH3 H

H C C C C H 2,3,3-trimethylbut-1-ene
(double bond is between carbon
CH3 H “1-2” and methyl group at
carbon “2,3,3”
Br H Br

Br C C C C Br 1,1,1,4,4,4-
hexabromobut-2-ene
Br H Br carbon “2-3” and six
bromine atoms at carbon “1,4” [email protected] 58
 H CH3 H H H

H C C C C C H

H CH3 H

4,4-dimethylpent-2-ene
(double bond between Carbon “2-3” and two methyl
group at carbon “4”)
H2C CHCH2 CH2 CH3 Pent -1- ene
( After drawing the structural formula the double bond is
between Carbon “1-2”
[email protected] 59
 H

H C H

H C CH3
3,4,5-trimethylhex-2- ene
H C CH3 (i)double bond between Carbon “2-
3,”
C CH3 (ii)three methyl groups at carbon
“3.4,5”)
C H

H C H
H [email protected] 60
 Br

Br C

C
1,1,6,6-tetrabromohex-1,2,3,4,5-
C
pentaene
(i)double bond between Carbon
C
“2-3, 3-4, 4-5, 5-6, 1-2,”
(ii)four Bromine groups at carbon
C
“1,1,6,6”)
C Br
Br [email protected] 61
.H2C C(CH3)C(CH3)2 CH2 CH3
2,3,3-trimethylpent -1- ene

H2C C(CH3)C(CH3)2 C(CH3)2 CH3

2,3,3,4,4-pentamethylpent -1- ene

H3C C(CH3)C(CH3) C(CH3)2 CH3

2,3,4,4-tetramethylpent -2- ene

H2C C(CH3)C(CH3) C(CH3) CH3

2,3,4-trimethylpent -1,3- diene

H2C CBrCBr CBr CH3

2,3,4-tribromopent -1,3- diene
[email protected] 62
H2C CHCH CH2
But -1,3- diene

Br2C CBrCBr CBr2

1,1,2,3,4,4-hexabromobut -1,3- diene

I2C CICI CI2

1,1,2,3,4,4-hexaiodobut -1,3- diene

H2C C(CH3)C(CH3) CH2

2,3-dimethylbut -1,3- diene

H2CCCH2
prop -1,2,- diene
[email protected] 63
(c)Occurrence and extraction
At indusrial level,alkenes are obtained from the
cracking of alkanes.
Cracking is the process of breaking long chain
alkanes to smaller/shorter alkanes, an alkene and
hydrogen gas at high temperatures.
Cracking is a major source of useful hydrogen gas
for manufacture of ammonia/nitric(V)acid/HCl
i.e.
Long chain alkane->shorter alkane+ Alkene+ Hydrogen

[email protected] 64
1.When irradiated with high energy radiation,
Propane undergo cracking to form methane gas,
ethene and hydrogen gas.
Chemical equation
CH3CH2CH3 (g) -> CH4(g) +CH2=CH2(g)+ H2(g)
2.Octane undergo cracking to form hydrogen gas,
butene and butane gases
Chemical equation
CH3(CH2) 6 CH3 (g) ->
CH3CH2CH2CH3(g)+CH3 CH2CH=CH2(g)+H2 (g)
[email protected] 65
 (d)School laboratory preparation of alkenes
In a school laboratory, alkenes may be prepared from
dehydration of alkanols using:
(i) concentrated sulphuric(VI)acid(H2SO4).
(ii)aluminium(III)oxide(Al2O3) i.e
Alkanol --Conc. H2SO4 --> Alkene + Water
Alkanol --Al2O3 --> Alkene + Water e.g.
1.(a)At about 180oC,concentrated sulphuric(VI)acid
dehydrates/removes water from ethanol to form ethene.
The gas produced contain traces of carbon(IV)oxide
and sulphur(IV)oxide gas as impurities.
It is thus passed through concentrated sodium
/potassium hydroxide solution to remove the impurities.
[email protected] 66
Chemical equation
CH3CH2OH (l)-conc H2SO4/180oC-->
CH2=CH2(g)+ H2O(l)
(b)On heating strongly aluminium(III)oxide(Al2O3),it
dehydrates/removes water from ethanol to form ethene.
Ethanol vapour passes through the hot aluminium (III)
oxide which catalyses the dehydration.
Activated aluminium(III)oxide has a very high affinity for
water molecules/elements of water and thus dehydrates/
removes water from ethanol to form ethene.
Chemical equation
CH3CH2OH (l) --(Al2O3/strong heat-->
[email protected] 67
CH2=CH2(g) + H2O(l)
2(a) Propan-1-ol and Propan-2-ol(position isomers of
propanol) are dehydrated by conc H2SO4 at about 180oC
to propene(propene has no position isomers).
Chemical equation
CH3CH2 CH2OH (l) -- conc H2SO4/180oC -->
CH3CH2=CH2(g) + H2O(l)
Propan-1-ol Prop-1-ene
CH3CHOH CH3 (l) -- conc H2SO4/180oC -->
CH3CH2=CH2(g) + H2O(l)
Propan-2-ol Prop-1-ene
(b) Propan-1-ol and Propan-2-ol(position isomers of
propanol) are dehydrated by heating strongly aluminium
(III)oxide(Al2O3) form propene [email protected] 68
Chemical equation
CH3CH2 CH2OH (l) -- Heat/Al2O3 -->
CH3CH2=CH2(g) + H2O(l)
Propan-1-ol Prop-1-ene
CH3CHOH CH3 (l) -- Heat/Al2O3 -->
CH3CH2=CH2(g) + H2O(l)
Propan-2-ol Prop-1-ene
3(a) Butan-1-ol and Butan-2-ol ( position isomers of
butanol ) are dehydrated by conc H2SO4 at about 180oC
to But-1-ene and But-2-ene respectively
Chemical equation
CH3CH2 CH2 CH2OH (l) -- conc H2SO4/180oC -->CH3
CH2CH2=CH2(g) + H2O(l)
[email protected] 69

Butan-1-ol But-1-ene
CH3CHOH CH2CH3 (l)-- conc H2SO4/180oC -->
CH3CH=CH CH2(g) + H2O(l)
Butan-2-ol But-2-ene
(b) Butan-1-ol and Butan-2-ol are dehydrated by
heating strongly aluminium (III) oxide (Al 2O3) form But-
1-ene and But-2-ene respectively.
Chemical equation
CH3CH2 CH2 CH2OH (l) -- Heat/Al2O3 -->
CH3 CH2CH2=CH2(g) + H2O(l)
Butan-1-ol But-1-ene
CH3CHOH CH2CH3 (l) -- Heat/Al2O3 -->
CH3CH=CH CH2(g) + H2O(l)
Butan-2-ol But-2-ene [email protected] 70
Laboratory set up for the preparation of alkenes/ethene
Caution:
(i)Ethanol is highly inflammable,
(ii)Conc H2SO4 is highly corrosive on skin contact.
Some broken porcelain or sand should be put in the flask
when heating to:
(i)prevent bumping which may break the flask.
(ii)ensure uniform and smooth boiling of the
mixture
The temperatures should be maintained at above160 oC.
At lower temperatures another compound -ether is
predominantly formed instead of ethene gas.
[email protected] 71
Preparation of ethene by dehydration of ethanol
(i) using Conc H2SO4

[email protected] 72
Preparation of ethene by dehydration of ethanol
(ii)using aluminium(III)oxide

[email protected] 73
(e)Properties of alkenes
I. Physical properties
Like alkanes, alkenes are colourless gases, solids and
liquids that are not poisonous.
They are slightly soluble in water.
The solubility in water decrease as the carbon chain/ molar
mass increase but very soluble in organic solvents like
tetrachloromethane and methylbenzene.
Melting/boiling point increase as carbon chain increase.
This is because of the increase in van-der-waals
/intermolecular forces as the carbon chain increase.
The 1st four straight chain alkenes (ethene,propene,but-1-
ene and pent-1-ene)are gases at room temperature/
pressure. [email protected] 74
Summary of physical properties of the 1st five alkenes
Alkane General formula Melting Boiling State at
point point room(298K)
(oC) (oC) temperature and
pressure
atmosphere
(101300Pa)
Ethene CH2CH2 -169 -104 gas
Propene CH3 CHCH2 -145 -47 gas
Butene CH3CH2 CHCH2 -141 -26 gas
Pent-1- CH3(CH2 CHCH2 -138 30 liquid
ene
Hex-1- CH3(CH2) CHCH2 -98 64 liquid
ene

[email protected] 75
 II. Chemical properties
(a)Burning/combustion
Alkenes burn with a yellow sooty/ smoky flame in excess
air to form carbon(IV) oxide and water.
In excess air/oxygen
Alkene + Air -> carbon(IV) oxide + water
In limited air
Alkenes burn with a yellow sooty/ smoky flame in
limited air to form carbon(II) oxide and water.
Alkene + Air -> carbon(II) oxide + water

[email protected] 76
Burning of alkenes with a yellow sooty/ smoky flame is
a confirmatory test for the presence of the =C=C=
double bond because they have higher C:H ratio.
A homologous series with = C = C= double or -C C-
triple bond is said to be unsaturated.

A homologous series with C C single bond is

said to be saturated.
Most of the reactions of the unsaturated compound

involve trying to be saturated to form a C C

single bond.

[email protected] 77
Examples of burning alkenes
1.(a) Ethene when ignited burns with a yellow sooty flame in
excess air to form carbon(IV) oxide and water.
Ethene + Air -> carbon(IV) oxide + water
C2H4(g) + 3O2(g) -> 2CO2(g) + 2H2O(l/g)
(b) Ethene when ignited burns with a yellow sooty flame in limited
air to form carbon(II) oxide and water.
Ethene + Air -> carbon(II) oxide +water
C2H4(g) + 3O2(g) -> 2CO2(g) + 2H2O(l/g)
2.(a) Propene when ignited burns with a yellow sooty flame in
excess air to form carbon(IV) oxide and water.
2C3H6(g) + 9O2(g)-> 6CO2(g) +6H2O(l/g)
(b) Propene when ignited burns with a yellow sooty flame in
limited air to form carbon(II) oxide and water.
C3H6(g)+ 3O2(g) -> 3CO(g) +3H2O(l/g)[email protected] 78
(b)Addition reactions
An addition reaction is one which an unsaturated compound reacts
to form a saturated compound.
Addition reactions of alkenes are named from the reagent used to
cause the addition/convert the double =C=C= to single bond.
(i)Hydrogenation
Hydrogenation is an addition reaction in which hydrogen
in presence of Nickel catalyst at high temperatures react
with alkenes to form alkanes.
Examples
1.When Hydrogen gas is passed through liquid vegetable
and animal oil at about 180oC in presence of Nickel
catalyst,solid fat is formed.
Hydrogenation is thus used to harden oils to solid fat
especially margarine. [email protected] 79
During hydrogenation, one hydrogen atom in the
hydrogen molecule attach itself to one carbon and the
other hydrogen to the second carbon breaking the double
bond to single bond.
Chemical equation
H2C=CH2 + H2 -Ni-> H3C - CH3

H H H H

C = C + H – H - Ni -> H-C – C-H

H H H H
2.Propene undergo hydrogenation to form Propane
Chemical equation
H3C CH=CH2 + H2 -Ni-> H3C CH2 - CH3 [email protected] 80
 H H H H H H

H C C = C + H – H - Ni/Pa->H - C – C - C- H

H H H H H
3.Both But-1-ene and But-2-ene undergo hydrogenation
to form Butane
But-1-ene + Hydrogen –Ni/Pa-> Butane
H3C CH2 CH=CH2 + H2 -Ni/Pa-> H3C CH2CH - CH3
H H H H H H H H

H C C - C = C+ H – H -Ni/Pa->H- C- C – C - C- H

H H H H H H H
[email protected] 81
 H H H H H H H H

H C C C C -H + H – H - Ni/Pa->H C -C– C - C- H

H H H H H H H
But-1,3-diene should undergo hydrogenation to form Butane. The
reaction uses two moles of hydrogen molecules/four hydrogen
atoms to break the two double bonds.
But-1,3-diene + Hydrogen –Ni/Pa-> Butane
H2C CH CH=CH2 + 2H2 -Ni/Pa-> H3C CH2CH - CH3
H H H H H H
H C C - C = C+ 2(H – H) -> H- C- C – C - C- H

H H H H H H H
[email protected] 82
(ii) Halogenation.
Halogenation is an addition reaction in which a halogen
(Fluorine, chlorine, bromine, iodine) reacts with an
alkene to form an alkane.
The double bond in the alkene break and form a single
bond.
The colour of the halogen fades as the number of moles
of the halogens remaining unreacted decreases/reduces.
One bromine atom bond at the 1st carbon in the double
bond while the other goes to the 2nd carbon.
Examples
1Ethene reacts with bromine to form 1,2-dibromoethane.
Chemical equation
H2C=CH2 + Br2 H2 Br C - CH2 Br
[email protected] 83
 H H H H

C = C + Br – Br -> H-C – C-H

H H Br Br
Ethene + Bromine 1,2-dibromoethane
2.Propene with chlorine forms 1,2-dichloropropane.
Chemical equation
H3C CH=CH2 + Cl2 H3C CHCl - CH2Cl
Propene + Chlorine 1,2-dichloropropane
H H H H H H

H - C - C = C – H + Cl – Cl H - C- C – C- H
[email protected] 84
H H Cl Cl
3.Both But-1-ene and But-2-ene undergo halogenation
with iodine to form 1,2-diiodobutane
Chemical equation
But-1-ene + iodine 1,2-diiodobutane
H3C CH2 CH=CH2 + I2 H3C CH2CH I - CH2I

H H H H H H H H

H C C - C = C + I– I -> H- C- C – C - C- H

H H H H H I I

But-2-ene + Fluorine 2,3-difluorobutane

H3C CH= CH-CH2 + F2 -> H3C CHFCHF - CH3
[email protected] 85
 H H H H H H H H

H C C C C -H + Br – Br -> H C -C– C - C- H

H H H Br Br H
But-1,3-diene should undergo using bromine to form 1,2,3,4-
tetrabutane. The reaction uses two moles of bromine molecules /
four bromine atoms to break the two double bonds.
But-1,3-diene + Bromine -> 1,2,3,-tetrabromobutane
H2C CH CH=CH2 + 2Br2 -> H3C CH2CH - CH3
H H H H H H
H C C - C = C+ 2(Br– Br) -> H- C- C – C - C- H

H H H Br Br Br Br
[email protected] 86
(iii) Reaction with hydrogen halides.
Hydrogen halides reacts with alkene to form a
halogenoalkane.
The double bond in the alkene break and form a single
bond.
The main compound is one which the hydrogen atom
bond at the carbon with more hydrogen .

Examples
1. Ethene reacts with hydrogen bromide to form
bromoethane.
Ethene + Bromine bromoethane
Chemical equation
H2C=CH2 + HBr H3 C - CH2 Br
[email protected] 87
 H H H H

C = C + H –Br -> H-C – C-H

H H Br H
Ethene + Hydrogen bromide bromoethane
2.Propene with hydrogen chloride forms 2-chloropropane.
Chemical equation
H3C CH=CH2 + HCl -> H3C CHCl - CH3
Propene + Chlorine -> 2-chloropropane
H H H H H H

H - C - C = C – H + H –Cl H - C- C – C- H
[email protected] 88
H H Cl H
3.Both But-1-ene and But-2-ene react with hydrogen
iodide to form 2-iodobutane
Chemical equation
But-1-ene + iodine -> 2-iodobutane
H3C CH2 CH=CH2 + HI ->H3C CH2CH I - CH3

H H H H H H H H

H C C - C = C + H– I -> H- C- C – C - C- H

H H H H H I H

But-2-ene + Fluorine 2-fluorobutane

H3C CH= CH-CH2 + HF -> H3C CHFCHF - CH3
[email protected] 89
 H H H H H H H H

H C C C C -H + H – F -> H C -C– C - C- H

H H H H Br H H
But-1,3-diene react with hydrogen bromide to form (as the main
product) 2,3-dibromobutane. The reaction uses two moles of
hydrogen bromide molecules to break the two double bonds.
But-1,3-diene + Bromine -> 2,3,-dibromobutane
H2C CH CH=CH2 + 2HBr -> H3C CHBrCH Br- CH3
H H H H H H
H C C - C = C+ 2(H –Br) -> H- C- C – C - C- H

H H H H Br Br H
[email protected] 90
 (iv) Reaction with bromine/chlorine water.
Chlorine and bromine water is formed when the
halogen is dissolved in distilled water.
Chlorine water has the formular HOCl
Bromine water has the formular HOBr
During the addition reaction .the halogen move to one
carbon and the OH to the other carbon in the alkene at the
=C=C= double bond to form a halogenoalkanol.
Bromine water + Alkene -> bromoalkanol
Chlorine water + Alkene -> chloroalkanol
Examples
[email protected] 91
 H H H H

C = C + HO – Br -> H-C – C-H

H H Br OH
Ethene + Bromine water bromoethanol
2.Propene with chlorine water forms 2-chloropropane or
chloropropan-2-ol.
Chemical equation
H3C CH=CH2 + HOCl -> H3C CHCl - CH2OH
Propene + Chlorine water -> 2-chloropropan-1-ol
H H H H H H

H - C - C = C – H + HO –Cl H - C- C – C- H
H H Cl OH
[email protected] 92
H3C CH=CH2 + HOCl -> H3C CHOH - CH2Cl
Propene + Chlorine water -> 1-chloropropan-2-ol
H H H H H H

H - C - C = C – H + HO –Cl H - C- C – C- H

H H OH Cl

3.Both But-1-ene and But-2-ene react with bromine

water to form 2-bromobutan-1-ol /3-bromobutan-2-ol
respectively
Chemical equation
I.But-1-ene + bromine water 2-bromobutan-1-ol
H3C CH2 CH=CH2+ HOBr H3C CH2CH Br - CH2OH
[email protected] 93
 H H H H H H H H

H C C C C -H + HO – Br -> H C -C– C - C- H

H H H H Br OH

But-2-ene + bromine water 3-bromobutan-2-ol

H3C CH= CHCH3 + HOBr H3C CH2OHCH Br CH3

H H H H H H H

H C C - C- C- H +HO – Br -> H - C - C– C - C- H

H H H H OH Br H
[email protected] 94
But-1,3-diene react with bromide to form (as the main
product) 2,3-dibromobutane.
The reaction uses two moles of bromine water molecules
to break the two double bonds.
But-1,3-diene + Bromine water ->
2,3,-dibromobutan-1,4-diol
H2C= CH CH=CH2+ 2HOBr ->
CH2OH CHBrCHBr CH2OH
H H H H
H

H - C = C - C = C+ 2(HO–Br) ->H- C- C – C - C- H

H H H H OH Br Br OH
[email protected] 95
(v) Oxidation.
Alkenes are oxidized to alkanols with duo/double functional
groups by oxidizing agents.
When an alkene is bubbled into orange acidified potassium
/sodium dichromate (VI) solution, the colour of the oxidizing agent
changes to green.
When an alkene is bubbled into purple acidified potassium /
sodium manganate(VII) solution the oxidizing agent is decolorized.
Examples
1Ethene is oxidized to ethan-1,2-diol by acidified
potassium/sodium manganate(VII) solution/ acidified
potassium/sodium dichromate(VI) solution.
The purple acidified potassium/sodium manganate(VII) solution is
decolorized.
The orange acidified potassium/sodium dichromate(VI) solution
turns to green. [email protected] 96
 H H H H

C = C + [O] in H+/KMnO4 ->H - C – C - H

H H OH OH
Ethene + [O] in H+/KMnO4 ethan-1,2-diol
2. Propene is oxidized to propan-1,2-diol
H3C CH=CH2 -[O] in H+/KMnO4->H3CCHOH -CH2OH
Propene --[O] in H+/KMnO4 --> propan-1,2-diol

H H H H H H

H - C - C = C – H + [O] H - C- C – C- H
H H OH OH
[email protected] 97
 H H H H H H H H

H C C C C -H + [O] -> H C -C– C - C- H

H H H H OH OH

But-1-ene + [O] in H+/KMnO4 -> butan-1,2-diol

But-2-ene + [O] in H+/KMnO4 -> butan-2,3-diol

H H H H H H H

H C C = C- C- H +[O] -> H - C - C– C - C- H

H H H H OH OH H
[email protected] 98
 (v) Hydrolysis.
Hydrolysis is the reaction of a compound with water/addition
of H-OH to a compound.
Alkenes undergo hydrolysis to form alkanols .This takes place
in two steps:
(i)Alkenes react with concentrated sulphuric(VI)acid at
room temperature and pressure to form alkylhydrogen
sulphate(VI).
Alkenes + concentrated sulphuric(VI)acid -> alkylhydrogen
sulphate(VI)
(ii)On adding water to alkylhydrogen sulphate(VI) then
warming, an alkanol is formed.
alkylhydrogen sulphate(VI) + water -warm-> Alkanol.
Examples
(i)Ethene reacts with cold concentrated sulphuric(VI)acid to
form ethyl hydrogen sulphate(VII) [email protected] 99
Examples
(i)Ethene reacts with cold concentrated sulphuric(VI)acid
to form ethyl hydrogen sulphate(VII)
Chemical equation
H2C=CH2 +H2SO4 -> CH3 - CH2OSO3H

H H H H

C = C + H2SO4 -> H-C – C-H

H H H OSO3H
(ii) Ethylhydrogen sulphate(VI) is hydrolysed by water
to ethanol
CH3 - CH2OSO3H +H2O -> CH3 - CH2OH + H2SO4
[email protected] 100
 H H H H

H - C - C - H + H2O -> H - C – C - H + H2SO4

H OSO3H H OH
2. Propene reacts with cold concentrated
sulphuric(VI)acid to form propyl hydrogen sulphate(VII)
Chemical equation
CH3CH=CH2 + H2SO4 -> CH3CH2 - CH2OSO3H
(ii) Propylhydrogen sulphate(VI) is hydrolysed by water
to propanol
Chemical equation
CH3 CH2CH2OSO3H +H2O -> CH3CH2OH + H2SO4
[email protected] 101
There are two types of polymerization:
(a)addition polymerization
(b)condensation polymerization
(a)addition polymerization
Addition polymerization is the process where a small
unsaturated monomer from alkene molecule join together
to form a large saturated molecule.

Only alkenes undergo addition polymerization.

Addition polymers are named from the alkene/monomer
making the polymer and adding the prefix “poly” before
the name of monomer to form a polyalkene
[email protected] 102
During addition polymerization
(i)the double bond in alkenes break
(ii)free radicals are formed
(iii)the free radicals collide with each other and join to
form a larger molecule.
The more collisions the larger the molecule.
Examples of addition polymerization
1.Formation of Polyethene
Polyethene is an addition polymer formed when ethene
molecule/monomer join together to form a large
molecule/polymer at high temperatures and pressure.
During polymerization:
(i)many molecules are brought nearer to each other by the
high pressure(reduce distance between reacting paticles)
[email protected] 103
 H H H H H H H H

C=C + C=C + C=C + C= C + …

H H H H H H H H
Ethene +Ethene+ Ethene+ Ethene + …
(ii)the double bond joining the ethane molecule break
to free radicals
H H H H H H H H

• C - C • + • C - C • + • C - C • + • C - C• + …

H H H H H H H H
Free ethene radical … [email protected] 104
 (iii)the free radicals collide with each other and join to
form a larger molecule

H H H H H H H H lone pair of electrons

• C – C - C – C - C – C - C - C• + …
H H H H H H H H
Lone pair of electrons can be used to join more
monomers to form longer polyethene.
Polyethene molecule can be represented as:
H H H H H H H H extension of
polymer
- C–C - C – C - C – C - C – C -
H H H H H H H H
[email protected] 105
Since the molecule is a repetition of one monomer, then the
polymer is:
H H

(C–C )n

H H
Where n is the number of monomers in the polymer.
The number of monomers in the polymer can be determined
from the molar mass of the polymer and monomer from the
relationship:
Number of monomers/repeating units in monomer
= Molar mass polymer
Molar mass monomer [email protected] 106
Examples
Polythene has a molar mass of 4760.Calculate the
number of ethene molecules in the polymer(C=12.0,
H=1.0 )
Number of monomers/repeating units in polymer
= Molar mass polymer =>Molar mass polyethene = 4760
Molar mass monomer Molar mass ethene (C2H4 )= 28
Substituting 4760 = 170 ethene molecules
28
The commercial name of polyethene is polythene. It is an
elastic, tough, transparent and durable plastic. Polythene
is used: (i)in making plastic bag
(ii)bowls and plastic bags
(iii)packaging [email protected] 107
c)Test for the presence of – C = C – double bond.
(i)Burning/combustion
All unsaturated hydrocarbons with a – C = C – or
– C = C – bond burn with a yellow sooty flame.
Experiment
Scoop a sample of the substance provided in a clean
metallic spatula. Introduce it on a Bunsen burner.
Observation Inference
Solid melt then burns with –C=C–
a yellow sooty flame
– C = C – bond

[email protected] 108
(ii)Oxidation by acidified KMnO4/K2Cr2O7

Bromine water ,Chlorine water and Oxidizing agents

acidified KMnO4/K2Cr2O7 change to unique colour in

presence of – C = C – or – C = C – bond.
Experiment
Scoop a sample of the substance provided into a clean
test tube.
Add 10cm3 of distilled water.
Shake.
Take a portion of the solution mixture.
Add three drops of acidified KMnO4/K2Cr2O7 .
[email protected] 109
 Observation
Inference
Acidified KMnO4 decolorized
Orange colour of acidified –C=C–
K2Cr2O7 turns green
Bromine water is decolorized – C = C – bond
Chlorine water is decolorized

(d)Some uses of Alkenes

1. In the manufacture of plastic
2. Hydrolysis of ethene is used in industrial manufacture
of ethanol.
3. In ripening of fruits.
4. In the manufacture of detergents. [email protected] 110
(iii) Alkynes
(a)Nomenclature/Naming
These are hydrocarbons with a general formula
CnH2n-2 and - C = C- triple bond as the
functional group .
n is the number of Carbon atoms in the molecule.
The carbon atoms are linked by at least one
triple bond to each other and single bonds to
hydrogen atoms.
They include:
[email protected] 111
n General/Molecular Structural formula Name
formula
2 C2H2 Ethyne
H C C H
3 C3H4 H Propyne
H C C C H
H
CH C CH3

4 C4H6 H H Butyne
H C C C C H
H H
CH C CH2CH3

5 C5H8 H H H Pentyne
H C C C C C H
H H H
CH C (CH2)2CH3
6 C6H10 H H H H Hexyne
H C C C C C C H
H H H H
CH C (CH2)3CH3 [email protected] 112
7 C7H12 H H H H H Heptyne
H C C C C C C C H
H H H H H H H
CH C (CH2)4CH3

8 C8H14 H H H H H H Octyne
H C C C C C C C C H
H H H H H H
CH C (CH2)5CH3

9 C9H16 H H H H H H H Nonyne
H C C C C C C C C C H
H H H H H H H
CH C (CH2)6CH3

10 C10H18 H H H H H H H H Decyne
H C C C C C C C C C C H
H H H H H H H H
CH C (CH2)7CH3
[email protected] 113
Note
1. Since carbon is tetravalent ,each atom of carbon in the alkyne
MUST always be bonded using four covalent bond /four shared
pairs of electrons including at the triple bond.

2. Since Hydrogen is monovalent ,each atom of hydrogen in the

alkyne MUST always be bonded using one covalent bond/one
shared pair of electrons.

3. One member of the alkyne ,like alkenes and alkanes, differ from
the next/previous by a CH2 group(molar mass of 14 atomic mass
units).
They thus form a homologous series.
e.g
Propyne differ from ethyne by (14 a.m.u) one carbon and two
Hydrogen atoms from ethyne. [email protected] 114
4.A homologous series of alkenes like that of alkanes:
(i) differ by a CH2 group from the next /previous consecutively
(ii) have similar chemical properties
(iii)have similar chemical formula with general formula C nH2n-2
(iv)the physical properties also show steady gradual change.

5.The - C = C - triple bond in alkyne is the functional group.

The functional group is the reacting site of the alkynes.

6. The - C = C - triple bond in alkyne can easily be broken to

accommodate more /four more monovalent atoms.
The - C = C - triple bond in alkynes make it thus unsaturated
like alkenes.

7. Most of the reactions of alkynes like alkenes take place at the -

C = C- triple bond. [email protected] 115
(b)Isomers of alkynes
Isomers of alkynes have the same molecular general formula but
different molecular structural formula.
Isomers of alkynes are also named by using the IUPAC
(International Union of Pure and Applied Chemistry) system of
nomenclature/naming.
The IUPAC system of nomenclature of naming alkynes uses the
following basic rules/guidelines:
1.Identify the longest continuous/straight carbon chain which
contains the - C = C- triple bond to get/determine the parent
alkene.
2. Number the longest chain form the end of the chain which
contains the -C = C- triple bond so as - C = C- triple bond get
lowest number possible.
[email protected] 116
3 Indicate the positions by splitting “alk-position-yne”
e.g. but-2-yne, pent-1,3-diyne.
4.The position indicated must be for the carbon atom at
the lower position in the -C = C- triple bond. i.e
But-2-yne means triple -C = C- at Carbon “2”and “3”
Pent-1,3-diyne means two triple bonds; one between
carbon “1” and “2”and between carbon “3” and “4”
5. Determine the position, number and type of branches.
Name them as methyl, ethyl, propyl e.tc. according to
the number of alkyl carbon chains attached to the alkyne.
Name them fluoro-,chloro-,bromo-,iodo- if they are
halogens
[email protected] 117
6.Use prefix di-,tri-,tetra-,penta-,hexa- to show the
number of triple - C = C- bonds and branches attached
to the alkyne.
7.Position isomers can be formed when the - C = C-
triple bond is shifted between carbon atoms e.g.
But-2-yne means triple - C = C- is between Carbon
“2”and “3”
But-1-yne means triple - C = C- is at Carbon “1”and “2”
But-1-yne and But-2-yne are position isomers of Butyne.
9. Like alkanes and alkynes , an alkyl group can be
attached to the alkyne. Chain/branch isomers are thus
formed.e.g.
Butyne and 2-methyl propyne both have the same general
formular but different branching chain.
[email protected] 118
Practice on IUPAC nomenclature of alkynes
H H

H C C C C H But-1-yne(triple bond is
between carbon “1-2”

H H

H H

H C C C C H But-2-yne(triple bond is
between carbon “2-3”

H H [email protected] 119
 CH3 H

H C C C C H 3-methylbut-1-yne(double
bond is between carbon
H H “3-4” and methyl group at
carbon “3”
H H

H C C C C H 1,4-dichlorobut-2-yne
(double bond is between
Cl Cl carbon “2-3” and
two chlorine atoms at carbon
“1&4” [email protected] 120
 H CH3 CH3 H

H C C C C H 2,3,3-trimethylbut-1-yne
(double bond is between carbon
CH3 H “1-2” and methyl group at
carbon “2,3,3”
Br H Br

Br C C C C Br 1,1,1,4,4,4-
hexabromobut-2-yne
Br H Br carbon “2-3” and six
bromine atoms at carbon “1,4”
[email protected] 121
 H CH3 H

H C C C C C H

H CH3 H

4,4-dimethylpent-2-yne
(triple bond between Carbon “2-3” and two methyl group
at carbon “4”)
H2C CHCH2 C CH Pent -1- yne
( After drawing the structural formula the triple bond is
between Carbon “1-2”
[email protected] 122
 H

H C H

H C CH3
4,5-dimethylhex-2- yne
H C CH3 (i)Triple bond between Carbon “2-3,”
(ii)two methyl groups at carbon
C “4,5”)

H C H
H [email protected] 123
Br

C
1,6-dibromohex-1,3,5-triyne
C
(i)triple bond between Carbon
“1-2, 3-4, 5-6,”
C
(ii)two Bromine atoms at carbon
“1,6”)
C

C
Br [email protected] 124
.H3C CH(CH3)C(CH3)2 CCH
3,3,4-trimethylpent -1- yne

HC C C(CH3)2 C(CH3)2 CH3

3,3,4,4-tetramethylpent -1- yne

H3C C(CH3) 2C C CH3

2,2-dimethylpent -2- yne

HC CC(CH3) 2 C CH3
3,3,-dimethylpent -1,4- diyne

BrC CC C CH3
1-bromopent -1,3- diyne
[email protected] 125
HC CC CH
But -1,3- diyne

BrC CBCB CBr

1,4-dibromobut -1,3- diyne

IC C C CI
1,4-diiodobut -1,3- diyne

HC C C(CH3) 2C(CH3) 2 CCH

3,3,4,4-tetramethylhex -1,6- dine

HCCCH
prop -1,2,- diyne [email protected] 126
(c)Preparation of Alkynes.
Ethyne is prepared from the reaction of water on calcium
carbide.
The reaction is highly exothermic and thus a layer of sand
should be put above the calcium carbide to absorb excess
heat to prevent the reaction flask from breaking.
Copper(II)sulphate(VI) is used to catalyze the reaction
[email protected] 127
(d)Properties of alkynes
I. Physical properties
Like alkanes and alkenes,alkynes are colourles gases,
solids and liquids that are not poisonous.
They are slightly soluble in water.
The solubility in water decrease as the carbon chain and
as the molar mass increase but very soluble in organic
solvents like tetrachloromethane and methylbenzene.
Ethyne has a pleasant taste when pure.
The melting and boiling point increase as the carbon chain
increase.
This is because of the increase in van-der-waals
/intermolecular forces as the carbon chain increase.
[email protected] 128
The 1st three straight chain alkynes (ethyne,propyne and
but-1-yne)are gases at room temperature and pressure.
The density of straight chain alkynes increase with
increasing carbon chain as the intermolecular forces
increases reducing the volume occupied by a given mass
of the alkyne.
Summary of physical properties of the 1st five alkenes
Alkyne General formula Melting Boiling State at room(298K)
point(oC) point(oC) temperature and
pressure atmosphere
(101300Pa)
Ethyne CH CH -82 -84 gas
Propyne CH3 C CH -103 -23 gas
Butyne CH3CH2 CCH -122 8 gas
Pent-1-yne CH3(CH2) 2 CCH -119 39 liquid
Hex-1-yne CH3(CH2) 3C CH -132 71 liquid
[email protected] 129
II. Chemical properties
(a)Burning/combustion
Alkynes burn with a yellow/ luminous very sooty/ smoky
flame in excess air to form carbon(IV) oxide and water.
Alkyne + Air -> carbon(IV) oxide +water

Alkenes burn with a yellow/ luminous verysooty/ smoky

flame in limited air to form carbon(II) oxide/carbon and
water.
Alkyne + Air -> carbon(II) oxide /carbon +water
Burning of alkynes with a yellow/ luminous very sooty/
smoky flame is a confirmatory test for the presence of
the - C = C – triple bond because they have very high
C:H ratio. [email protected] 130
Examples of burning alkynes
1.(a) Ethyne when ignited burns with a yellow very sooty
flame in excess air to form carbon(IV) oxide and water.
Ethyne + Air -> carbon(IV) oxide + water
Excess air/oxygen
2C2H2(g)+ 5O2(g)-> 4CO2(g) + 2H2O(l/g)
(b) Ethyne when ignited burns with a yellow sooty
flame in limited air to form a mixture of unburnt carbon
and carbon(II) oxide and water.
Limited air
Ethyne + Air -> carbon(II) oxide + carbon + water
C2H2(g)+ O2(g) -> 2CO2(g) + C +2H2O(l/g)

[email protected] 131
2.(a) Propyne when ignited burns with a yellow sooty
flame in excess air to form carbon(IV) oxide and water.

Excess air/oxygen
Propyne + Air -> carbon(IV) oxide + water
C3H4(g) + 4O2(g)-> 3CO2(g) +2H2O(l/g)
(a) Propyne when ignited burns with a yellow sooty
flame in limited air to form carbon(II) oxide and water.

Limited air
Propene + Air -> carbon(IV) oxide +water
2C3H4(g) + 5O2(g) -> 6CO(g) + 4H2O(l/g)

[email protected] 132
(b)Addition reactions

An addition reaction is one which an unsaturated

compound reacts to form a saturated compound.
Addition reactions of alkynes are also named from the
reagent used to cause the addition/convert the triple
-C = C- to single C- C bond
(i)Hydrogenation
Hydrogenation is an addition reaction in which hydrogen
in presence of Palladium/Nickel catalyst at 150oC
temperatures react with alkynes to form alkenes then
alkanes.
[email protected] 133
Examples
1.During hydrogenation, two hydrogen atom in the
hydrogen molecule attach itself to one carbon and the
other two hydrogen to the second carbon breaking the
triple bond to double the single.
Chemical equation

HC = CH+H2 -Ni/Pa ->H2C = CH2+H2 -Ni/Pa ->H3C-CH3

H H H H H H

C = C+H–H-Ni/Pa-> C =C + H–H -Ni/Pa -> H-C - C–H

[email protected] 134

H H H H
2.Propyne undergo hydrogenation to form Propane
Chemical equation
H3C CH=CH2 + 2H2 -Ni/Pa-> H3C CH - CH3

H H H H H H

H C C = C + 2H – H - Ni/Pa-> H - C – C - C- H

H H H H H
3.Both But-1-yne and But-2-yne undergo hydrogenation
to form Butane
Chemical equation
But-1-yne + Hydrogen –Ni/Pa-> Butane
H3C CH2 C = CH + 2H2 -Ni/Pa-> H3C CH2CH2 - CH3
[email protected] 135
(ii) Halogenation.
Halogenation is an addition reaction in which a halogen
(Fluorine, chlorine, bromine, iodine) reacts with an
alkyne to form an hallogenoalkene then halogenoalkane.
The reaction of alkynes with halogens is faster than with
alkenes.
The triple bond in the alkyne break and form a double
then single bond.
The colour of the halogen fades as the number of moles
of the halogens remaining unreacted decreases.
Two bromine atoms bond at the 1st carbon in the triple
bond while the other two goes to the 2nd carbon.
Examples
[email protected] 136
 H H H H

C = C + 4Br – Br -> Br - C – C - Br

H H Br Br
Ethyne + Bromine 11,2,2-tetrabromoethane
2.Propyne with chlorine forms 1,2-tetrachloropropane.
Chemical equation
H3C C = CH + 2Cl2 -> H3C CCl2 - CH Cl2
Propyne + Chlorine 1,1,2,2-terachloropropane
H H Cl Cl

H - C - C = C – H + 4Cl – Cl H - C- C – C- H
[email protected] 137
H H Cl Cl
3.Both But-1-yne and But-2-yne undergo halogenation
with iodine to form 1,1,2,2-tetraiodobutane
Chemical equation
But-1-yne + iodine -> 1,1,2,2-tetraiodobutane
H3C CH2 C = CH + 2I2 -> H3C CH2CI2 - CH I2

H H H H I I

H C C - C = C + 4I– I -> H- C- C – C - C- H

H H H H H I I

But-2-yne + Fluorine -> 2,2,3,3-tetrafluorobutane

H3C C= C-CH3 + 2F2 -> H3C CF2CF2 - CH3 [email protected] 138
 H H H Br Br H

H C C C C -H + 4Br – Br -> H C -C– C - C- H

H H H Br Br H
But-1,3-diyne should undergo halpgenation using bromine to form
1,1,2,2,3,3,4,4-octabromobutane. The reaction uses four moles of bromine
molecules / eight bromine atoms to break the two triple bonds.
But-1,3-diene + Bromine -> 1,1,2,2,3,3,4,4-octabromobutane.
H2C CH CH=CH2 + 4Br2 -> H3C CH2CH - CH3
H Br Br Br Br
H C C - C = C+ 4(Br– Br) -> H- C- C – C - C- H

Br Br Br Br
[email protected] 139
(iii) Reaction with hydrogen halides.
Hydrogen halides reacts with alkyne to form a
halogenoalkene then halogenoalkane.
The triple bond in the alkyne break and form a double
then single bond.
The main compound is one which the hydrogen atom
bond at the carbon with more hydrogen .

Examples
1. Ethyne reacts with hydrogen bromide to form
dibromoethane.
Ethyne + Bromine dibromoethane
Chemical equation
HC = CH + 2HBr H3 C - CH Br2
[email protected] 140
 H H H H

C = C + 2Br – H -> Br - C – C - H

H H Br H
Ethyne + Hydrogen bromide 1,1-dibromoethane
2.Propyne with hydrogen chloride forms 2,2-dichloropropane.
Chemical equation
H3C CH = CH2 + 2HCl -> H3C CHCl - CH3
Propyne + Chlorine -> 2,2-dichloropropane
H H Cl H

H - C - C = C – H + 2Cl – H H - C- C – C- H
H H Cl H
[email protected] 141
3.Both But-1-yne and But-2-yne react with hydrogen
iodide to form 2-iodobutane
Chemical equation
But-1-yne + hydrogen iodide -> 2,2-diiodobutane
H3C CH2 C = CH + 2HI ->H3C CH2C I2 - CH3

H H H H H H I H

H C C - C = C + 2H– I -> H- C- C – C - C- H

H H H H H I H

But-2-yne + hydrogen fluorine -> 2,2-difluorobutane

H3CC = C-CH3 + 2HF -> H3C CHF2CH2 - CH3
[email protected] 142
 H H H F H H

H C C C C -H + 2H – F -> H C -C– C - C- H

H H H F H H
But-1,3-diene react with hydrogen bromide to form (as the main
product) 2,2,3,3-tetrabromobutane. The reaction uses four moles of
hydrogen bromide molecules to break the two triple bonds.
But-1,3-diene + Bromine -> 2,2,3,3-tetrabromobutane
H2C CH CH = CH2 + 4HBr -> H3C CBr2CBr2CH3
H H Br Br H
H C C - C = C+ 4(Br– H) -> H- C- C – C - C- H

H Br Br H
[email protected] 143
[email protected] 144
[email protected] 145
(c)Test for the presence of – C = C –triple bond.
(i)Burning/combustion
Alkynes like aklkenes are unsaturated. They have the
– C = C– triple bond burn with a yellow sooty flame.
Experiment
Scoop a sample of the substance provided in a clean
metallic spatula. Introduce it on a Bunsen burner.
Observation Inference
Solid melt then burns with a – C = C –
yellow sooty flame
– C = C – bond
(ii)Oxidation by acidified KMnO4/K2Cr2O7
Bromine water ,Chlorine water and Oxidizing agents acidified
KMnO4/K2Cr2O7 change to unique colour in presence of – C = C -
[email protected] 146
 Experiment
Scoop a sample of the substance provided into a clean
test tube. Add 10cm3 of distilled water. Shake. Take a
portion of the solution mixture. Add three drops of
acidified KMnO4/K2Cr2O7 .
Observation
Inference
Acidified KMnO4 decolorized
Orange colour of acidified K2Cr2O7 – C = C –
turns green
Bromine water is decolorized – C = C – bond
Chlorine water is decolorized

[email protected] 147
 Legal caution!!!
Do not encourage your
institution to be a user
consumer of pirated soft wares.
Legal action can easily be taken
against both you and the
institution at your cost!!!
[email protected] 148
 ORGANIC
CHEMISTRY II
ALKANOLS, ALKANOIC
ACIDS AND POLYMERS.

[email protected] 149
(A).ALKANOLS.
(A). INTRODUCTION.
Alkanols belong to a homologous series of organic
compounds with a general formula CnH2n +1OH and thus
have the -OH as the functional group .
The 1st ten alkanols include:-

n General Structural formula IUPAC

/molecular name
formular
1 CH3OH H–C–O-H Methanol
│
H

[email protected] 150
2 CH3 CH2OH H H Ethanol
C2H5 OH
H C – C –O - H
│
H H

3 CH3 (CH2)2OH H H H Propan-1-ol

C3H7 OH
H - C – C - C –O - H
│
H H H

4 CH3 (CH2)3OH H H H H Butan-1-ol

C4H9 OH
H C – C - C - C –O - H
│
H H H H

[email protected] 151
 CH3(CH2)4OH H H H H H
5 C5H11 OH Pentan-1-ol
H C – C - C- C- C – O - H
│
H H H H H

6 CH3(CH2)5OH H H H H H H Hexan-1-ol
C6H13 OH
H C – C - C- C- C– C - O - H
│
H H H H H H

7 CH3(CH2)6OH Heptan-1-
C7H15 OH H H H H H H H ol

H C – C - C- C- C– C –C- O - H
│
H H H H H H H [email protected] 152
8 CH3(CH2)7OH H H H H H H H H Octanol
C8H17 OH
H C – C - C- C- C– C –C- C -O - H
│
H H H H H H H H

9 CH3(CH2)8OH H H H H H H H H H Nonanol
C9H19 OH
H C – C - C- C- C– C –C- C –C- O - H
│
H H H H H H H H H

10 CH3(CH2)9OH H H H H H H H H H H Decanol
C10H21 OH
H C – C - C- C- C– C –C- C –C- C- O -
H
│
H H H H H H H H H H

[email protected] 153
Alkanols like Hydrocarbons( alkanes/alkenes/alkynes)
form a homologous series where:
(i).general name is derived from the alkane name then
ending with “-ol”
(ii).the members have –OH as the functional group
(iii).they have the same general formula represented by
R-OH where R is an alkyl group.
(iv).each member differ by –CH2 group from the
next/previous.
(v).they show a similar and gradual change in their
physical properties e.g. boiling and melting points.
(vi).they show similar and gradual change in their
chemical properties.
[email protected] 154
 B. ISOMERS OF ALKANOLS.
Alkanols exhibit both structural and positional
isomerism.
The isomers are named by using the following
basic guidelines:
(i).Like alkanes , identify the longest carbon
chain to be the parent name.
(ii).Identify the position of the -OH functional
group to give it the smallest /lowest position.
(iii).Identify the type and position of the side
branches.
Practice examples of isomers of alkanols
[email protected] 155
(i).Isomers of propanol C3H7OH
CH3CH2CH2O-H - Propan-1-ol
O-H

CH3CHCH3 - Propan-2-ol

Propan-2-ol and Propan-1-ol are positional isomers

because only the position of the – OH functional group
changes.

[email protected] 156
(ii).Isomers of Butanol C4H9OH

1. CH3 CH2 CH3 CH2 OH Butan-1-ol

2. CH3 CH2 CH CH3

OH Butan-2-ol
CH3

3. CH3 C CH3

OH 2-methylpropan-2-ol
Butan-2-ol and Butan-1-ol are positional isomers because
[email protected] 157
only the position of the -OH functional group changes.
2-methylpropan-2-ol is both a structural and positional
isomers because both the position of the functional group
and the arrangement of the atoms in the molecule
changes.
(iii).Isomers of Pentanol C5H11OH
CH3 CH2 CH2CH2CH2 OH Pentan-1-ol
(Positional isomer)

CH3CH2 CH CH3

OH Pentan-2-ol
(Positional isomer)
[email protected] 158
CH3 CH2 CH CH2 CH3

OH Pentan-3-ol
(Positional isomer)

CH3

CH3 CH2 CH2 C CH3

OH 2-methylpentan-2-ol
(Positional /structural isomer)
[email protected] 159
C. LABORATORY PREPARATION OF ALKANOLS.
For decades the world over, people have been fermenting
grapes juice, sugar, carbohydrates and starch to produce
ethanol as a social drug for relaxation.
In large amount, drinking of ethanol by mammals /human
beings causes mental and physical lack of coordination.
Prolonged intake of ethanol causes permanent mental and
physical lack of coordination because it damages vital
body organs like the liver.
Fermentation is the reaction where sugar is converted to
alcohol/alkanol using biological catalyst/enzymes in
yeast.
It involves three processes:
[email protected] 160
 (i).Conversion of starch to maltose using the enzyme diastase

(C6H10O5)n(s)+H2O(l) ---diastase enzyme---> C12H22O11(aq)

(Starch) (Maltose)

(ii).Hydrolysis of Maltose to glucose using the enzyme

maltase.

C12H22O11(aq) + H2O(l)----maltase enzyme---> 2C6H12O6(aq)

(Maltose) (Glucose)

(iii).Conversion of glucose to ethanol and carbon(IV)oxide gas

using the enzyme zymase.

C6H12O6(aq) -- zymase enzyme ---> 2C2H5OH(aq) + 2CO2(g)

(Glucose) (Ethanol)
[email protected] 161
 At concentration greater than 15% by volume, the ethanol
produced kills the yeast enzymes stopping the reaction.
To increases the concentration, fractional distillation is
done to produce spirits (e.g. Brandy=40% ethanol).
Methanol is much more poisonous /toxic than ethanol.
If it is taken in large quantity, it causes instant blindness
and liver damage, killing the consumer victim within
hours.
School laboratory preparation of ethanol from fermentation of
glucose
Measure 100cm3 of pure water into a conical flask.
Add about five spatula end full of glucose. Stir the mixture to
dissolve. Add about one spatula end full of yeast.
Set up the apparatus as below.
[email protected] 162
 Preserve the mixture for about three days.
D.PHYSICAL AND CHEMICAL PROPERTIES OF
ALKANOLS
Characteristic properties of alkanols
•Role of yeast
Yeast is a single cell fungus which contains the enzyme
maltase and zymase that catalyse the fermentation process.

•Observations in lime water.

A white precipitate is formed that dissolve to a
colourless solution later. Lime water/Calcium hydroxide
reacts with carbon(IV)0xide produced during the
fermentation to form insoluble calcium carbonate and
water. [email protected] 163
 More carbon (IV)0xide produced during fermentation
react with the insoluble calcium carbonate and water to
form soluble calcium hydrogen carbonate.
Ca(OH)2(aq) + CO2 (g)----------> CaCO3(s)+ H2O(l) then
CO2 (g)+ CaCO3(s) + H2O(l) ---------> Ca(HCO3) 2 (aq)
(c).Effects on litmus paper
Experiment.
Take the prepared sample and test with both blue and red
litmus papers.
Repeat the same with pure ethanol and methylated spirit.

Sample Observation table.

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Substance/alkanol Effect on litmus paper
Prepared sample Blue litmus paper remain blue
Red litmus paper remain red
Absolute ethanol Blue litmus paper remain blue
Red litmus paper remain red
Methylated spirit Blue litmus paper remain blue
Red litmus paper remain red
Explanation
Alkanols are neutral compounds/solutions/liquids that
have characteristic sweet smell and taste.
They have no effect on both blue and red litmus papers.
(d).Solubility in water.
Experiment.
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 Place about 5cm3 of prepared sample into a clean test tube.
Add equal amount of distilled water.
Repeat the same with pure ethanol and methylated spirit.
Observation.
No layers formed between the two liquids.
Explanation.
Ethanol is miscible in water.
Both ethanol and water are polar compounds.
The solubility of alkanols decrease with increase in the alkyl
chain/molecular mass.
The alkyl group is insoluble in water while – OH functional group
is soluble in water.
As the molecular chain becomes longer ,the effect of the alkyl
group increases as the effect of the functional group decreases.

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(e).Melting/boiling point.
Experiment.
Place pure ethanol in a long boiling tube .Determine its
boiling point.
Observation.
Pure ethanol has a boiling point of 78 oC at sea level/one
atmosphere pressure.
Explanation.
The melting and boiling point of alkanols increase with
increase in molecular chain/mass .
This is because the intermolecular/van-der-waals forces
of attraction between the molecules increase.
More heat energy is thus required to weaken the longer
chain during melting and break during boiling.
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(f).Density.
Density of alkanols increase with increase in
the intermolecular/van-der-waals forces of
attraction between the molecules, making them
move very close to each other.
This reduces the volume occupied by the
molecules and thus increase their mass per unit
volume (density).
Summary table showing the trend in physical
properties of alkanols

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(g).Burning
Experiment.
Place the prepared sample in a watch glass. Ignite.
Repeat with pure ethanol and methylated spirit.
Observation/Explanation.
Fermentation produce ethanol with a lot of water(about
a ratio of 1:3) which prevent the alcohol from igniting.
Pure ethanol and methylated spirit easily catch fire,ie are
highly flammable.
They burn with an almost colourless non-sooty/non-
smoky blue flame to form carbon (IV) oxide (in excess
air/oxygen) or carbon(II) oxide (in limited air) and
water.
Ethanol is thus a saturated compound like alkanes.
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[email protected] 170
Alkanol Melting Boiling Density Solubility in
point point gcm-3 water
(oC) (oC)
Methanol -98 65 0.791 soluble
Ethanol -117 78 0.789 soluble
Propanol -103 97 0.803 soluble
Butanol -89 117 0.810 Slightly soluble
Pentanol -78 138 0.814 Slightly soluble
Hexanol -52 157 0.815 Slightly soluble
Heptanol -34 176 0.822 Slightly soluble
Octanol -15 195 0.824 Slightly soluble
Nonanol -7 212 0.827 Slightly soluble
Decanol 6 228 0.827 Slightly soluble
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C2H5OH(l) + 3O2 (g) ----> 3H2O(l) + 2CO2(g) (excess air)
C2H5OH(l)+2O2(g) ---> 3H2O(l) +2CO(g) (limited air)
2CH3OH(l)+3O2(g) --> 4H2O(l) +2CO2(g) (excess air)
2CH3OH(l) +2O2(g)---> 4H2O(l) + 2CO(g) (limited air)
2C3H7OH(l) +9O2(g)---> 8H2O(l) +6CO2(g) (excess air)
C3H7OH(l) +3O2(g) ---> 4H2O(l) +3CO(g) (limited air)
2C4H9OH(l) +13O2(g)--> 20H2O(l) +8CO2(g) (excess air)
C4H9OH(l) +3O2(g)---> 4H2O(l) +3CO(g) (limited air)
Due to its flammability, ethanol is used;
(i).as a fuel in spirit lamps.
(ii).as gasohol when blended with gasoline.
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 (h).Formation of alkoxides.

Experiment.
Cut a very small piece of sodium.
Put it in a beaker containing about 20cm 3 of
the prepared sample in a beaker.
Test the products with litmus papers.
Repeat with absolute ethanol and methylated
spirit.
Sample observations.

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Substance/alkanol Effect of adding sodium
Fermentation (i).effervescence/fizzing/bubbles.
prepared sample (ii).colourless gas that extinguishes a
burning splint with “Pop” sound.
(iii).colourless solution formed.
(iv).blue litmus paper remain blue.
(v).red litmus paper turn blue.
Pure/absolute (i)sloweffervescence/fizzing/bubbles
ethanol/methylated (ii).colourless gas that extinguish
spirit burning splint with “Pop” sound is
produced slowly.
(iii).colourless solution is formed.
(iv).blue litmus paper remain blue.
(v).red litmus paper turn blue.
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Explanations.
Sodium/potassium reacts slowly with alkanols to form
basic solutions called alkoxides and producing hydrogen
gas.If the alkanol has some water the metals react faster
with the water to form soluble hydroxides/alkalis i.e.
Sodium + Alkanol ---> Sodium alkoxides + Hydrogen gas
Potassium+Alkanol->Potassium alkoxides+Hydrogen gas
Sodium +Water --->Sodium hydroxides + Hydrogen gas
Potassium+Water->Potassium hydroxides+ Hydrogen gas
Examples

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1.Sodium metal reacts with ethanol to form sodium
ethoxide.
Sodium metal reacts with water to form sodium
Hydroxide.
2CH3CH2OH(l) +2Na(s) ---> 2CH3CH2ONa (aq) + H2(g)
2H2O(l) + 2Na(s) ---------> 2NaOH(aq) + H2(g)
2.Potassium metal reacts with ethanol to form Potassium
ethoxide.
Potassium metal reacts with water to form Potassium
Hydroxide.
2CH3CH2OH(l) +2K(s)-----> 2CH3CH2OK(aq) + H2(s)
2H2O(l) + 2K(s) --------> 2KOH(aq) + H2(s)

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3.Sodium metal reacts with propanol to form sodium
propoxide.
Sodium metal reacts with water to form sodium
Hydroxide.
2C3H7OH(l) + 2Na(s) -----> 2C3H7ONa(aq) + H2(s)
2H2O(l) + 2Na(s)------> 2NaOH(aq) + H2(s)
4.Potassium metal reacts with propanol to form
Potassium propoxide.
Potassium metal reacts with water to form Potassium
Hydroxide.
2C3H7OH(l) + 2K(s)----> 2C3H7OK(aq) + H2(s)
2H2O(l) + 2K(s) --------> 2KOH(aq) + H2(s)

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5.Sodium metal reacts with butanol to form sodium
butoxide.
Sodium metal reacts with water to form sodium
Hydroxide.
2C4H9OH(l) + 2Na(s) ----> 2C4H9ONa(aq) + H2(g)
2H2O(l) + 2Na(s)------> 2NaOH(aq) + H2(g)

(i).Formation of Esters/Esterification.
Experiment.
Place 2cm3 of ethanol in a boiling tube. Add an equal
amount of ethanoic acid. To the mixture, carefully add
2drops of concentrated sulphuric (VI) acid and warm/heat
the mixture gently.
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 Pour the mixture into a beaker containing about
50cm3 of cold water. Smell the products. Repeat with
methanol.
Sample observations.
Substance/alkanol Effect on adding an equal amount
of ethanol and 2drops of
concentrated sulphuric (VI) acid.
Absolute ethanol Sweet fruity smell.
Methanol Sweet fruity smell.
Explanation.
Alkanols react with alkanoic acids to form sweet
fruity smelling compounds called Esters, and water. This
reaction/process is called Esterification and is catalyzed
by concentrated sulphuric (VI) acid . [email protected] 179
Esters derive their names from the reacting alkanol and alkanoic
acid. The alkanol “becomes” an alkyl group and the alkanoic acid
“becomes” alkanoate hence alkylalkanoate. e.g.
Ethanol + Ethanoic acid --------> Ethylethanoate + Water
Ethanol + Propanoic acid ------> Ethylpropanoate + Water
Ethanol + Methanoic acid -------> Ethylmethanoate + Water
Ethanol + Butanoic acid ---------> Ethylbutanoate + Water
Propanol + Ethanoic acid---------->Propylethanoate + Water
Methanol + Ethanoic acid-------->Methylethanoate + Water
Methanol + Decanoic acid-------->Methyldecanoate + Water
Decanol + Methanoic acid ------>Decylmethanoate + Water
During the formation of the ester, the “O” joining the alkanol and
alkanoic acid comes from the alkanol.
R1-COOH + R2 – OH -------> R1 -COO – R2 + H2O
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Alkanol + Alkanoic acid-------Conc.H2SO4-------> Ester + water
Naturally esterification is catalyzed by sunlight.
Each ester has a characteristic sweet unique smell derived from the
many possible combinations of alkanols and alkanoic acids that
create a variety of known natural (mostly in fruits) and
synthetic(mostly in juices) esters . e.g.
1. Ethanol reacts with ethanoic acid to form the ester
ethylethanoate and water.
Ethanol+Ethanoic acid------------->Ethylethanoate +Water

C2H5OH(l)+CH3COOH(l)----> CH3COOC2H5(aq)+ H2O(l)

CH3CH2OH(l) + CH3COOH(l) --Conc. H2SO4 -->
CH3COOCH2CH3(aq)+H2O(l)
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 2. Ethanol reacts with propanoic acid to form the ester
ethylpropanoate and water.
Ethanol + Propanoic acid --Conc. H2SO4 -->
Ethylpropanoate + Water
C2H5OH (l)+ CH3CH2COOH(l) --Conc. H2SO4 -->
CH3CH2COOC2H5(aq) + H2O(l)
CH3CH2OH (l)+ CH3CH2COOH(l)--Conc.H2SO4 -->
CH3CH2COOCH2CH3(aq) +H2O(l)
3. Methanol reacts with ethanoic acid to form the ester
methyl ethanoate and water.
Methanol + Ethanoic acid --Conc. H2SO4 -->
Methylethanoate + Water
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 CH3OH(l) + CH3COOH(l) --Conc.H2SO4 -->
CH3COO CH3(aq) + H2O(l)
4. Methanol reacts with propanoic acid to form the ester
methyl propanoate and water.
Methanol + propanoic acid --Conc. H2SO4 -->
Methylpropanoate + Water
CH3OH(l)+ CH3CH2COOH(l) --Conc.H2SO4 -->
CH3CH2COOCH3(aq) + H2O(l)
5. Propanol reacts with propanoic acid to form the ester
propylpropanoate and water.
C3H7OH(l) + CH3CH2COOH(l) --Conc.H2SO4 -->
CH3CH2COOC3H7(aq) + H2O(l)
CH3CH2CH2OH(l)+ CH3 CH2COOH(l) --Conc. H2SO4 -->
[email protected] 183
 (j).Oxidation.
Experiment.
Place 5cm3 of absolute ethanol in a test tube.
Add three drops of acidified potassium manganate(VII).Shake
thoroughly for one minute/warm.
Test the solution mixture using pH paper.
Repeat by adding acidified potassium dichromate(VI).
Sample observation table.
Substance/ Adding acidified pH of Nature of
alkanol KMnO4/K2Cr2O7 resulting resulting
solution/mi solution/mixture
xture
Pure ethanol (i).Purple colour of pH= 4/5/6 Weakly acidic
KMnO4 decolorized pH = 4/5/6 Weakly acidic
(ii). Orange colour
of K2Cr2O7turns
184
green. [email protected]
 Explanation.
Both acidified KMnO4 and K2Cr2O7 are oxidizing
agents(add oxygen to other compounds). They oxidize
alkanols to a group of homologous series called alkanals
then further oxidize them to alkanoic acids. The oxidizing
agents are themselves reduced hence changing their
colour:
(i).Purple KMnO4 is reduced to colourless Mn2+ ions.
(ii).Orange K2Cr2O7is reduced to green Cr3+ ions.
The pH of alkanoic acids show they have few H+
because they are weak acids i.e
Alkanol + [O] -->Alkanal +[O] ---> alkanoic acid
NB. The [O] comes from the oxidizing agents,
acidified KMnO4 or K2Cr2O7 [email protected] 185
Examples.
1.When ethanol is warmed with three drops of acidified
KMnO4 ,there is decolorization of KMnO4.
Ethanol + [O] ---> Ethanal + [O] -----> Ethanoic acid.
CH3CH2OH + [O]---> CH3CH2O + [O]-----> CH3COOH.

2.When methanol is warmed with three drops of acidified

K2Cr2O7 ,the orange colour of acidified K2Cr2O7 changes
to green.
Methanol + [O]--> Methanal + [O] --> Methanoic acid.
CH3OH +[O] ---> CH3O + [O] --> HCOOH.

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3.When propanol is warmed with three drops of acidified
K2Cr2O7 ,the orange colour of acidified K2Cr2O7 changes to
green.
Propanol + [O]--> Propanal + [O] ---> Propanoic acid.
CH3CH2CH2OH + [O] ---> CH3CH2 CH2O + [O] ----->
CH3CH2COOH.

4.When butanol is warmed with three drops of acidified

K2Cr2O7 ,the orange colour of acidified K2Cr2O7 changes to
green.
Butanol + [O]---> Butanal + [O] ---> Butanoic acid.
CH3CH2CH2CH2OH + [O] -->CH3CH2CH2CH2O +[O]-->
CH3CH2COOH.
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 NB. Air slowly oxidizes ethanol to dilute ethanoic acid
commonly called vinegar.
If beer is not tightly corked, a lot of carbon (IV) oxide
escapes and there is slow oxidation of the beer making it
“flat”.
(k).Hydrolysis /Hydration and Dehydration.

(I). Hydrolysis/Hydration is the reaction of a

compound/substance with water.
Alkenes react with water vapour/steam at high
temperatures and high pressures in presence of
phosphoric (V) acid catalyst to form alkanols. i.e.
Alkenes+ Water ---- H3PO4 catalyst---->Alkanol.
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Examples.
(i).Ethene is mixed with steam over a phosphoric acid
catalyst at 300oC temperature and 60 atmosphere pressure to
form ethanol
Ethene + water ---60 atm/300oC/ H3PO4 --> Ethanol.
H2C =CH2 (g) + H2O(l) --60 atm/300oC/ H3PO4 --->

CH3CH2OH(l)
This is the main method of producing large quantities of
ethanol instead of fermentation.
(ii).Propene + water ---60 atm/300oC/ H3PO4 --> Propanol
CH3C =CH2(g) + H2O(l) ---H3PO4 --> CH3CH2CH2OH(l)
(iii).Butene+ water ---60 atm/300oC/ H3PO4 --> Butanol
CH3 CH2 C=CH2(g) +H2O(l) -->CH3CH2CH2CH2OH(l)
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 (II). Dehydration is the process by which concentrated
sulphuric (VI) acid (dehydrating agent) removes water
from a compound/substance.
Concentrated sulphuric (VI) acid dehydrates alkanols to
the corresponding alkenes at about 180oC. i.e
Alkanol --Conc. H2 SO4/180oC--> Alkene + Water
Examples.
(i).At 180oC and in presence of Concentrated sulphuric
(VI) acid, ethanol undergoes dehydration to form ethene.
Ethanol -------180oC/ H2SO4 ------> Ethene + Water
CH3CH2OH(l) ---180oC/ H2SO4 --->H2C=CH2(g)+ H2O(l)
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2. Propanol undergoes dehydration to form propene.
Propanol ---180oC/ H2SO4 --> Propene + Water
CH3 CH2 CH2OH(l) --180oC/ H2SO4 -->
CH3CH =CH2 (g) + H2O(l)
3. Butanol undergoes dehydration to form Butene.
Butanol ---180oC/ H2SO4 --> Butene + Water
CH3 CH2 CH2CH2OH(l) --180oC/ H2SO4 -->
CH3 CH2C =CH2 (g) + H2O(l)

3. Pentanol undergoes dehydration to form Pentene.

Pentanol ---180oC/ H2SO4 --> Pentene + Water
CH3 CH2 CH2 CH2 CH2OH(l)--180oC/ H2SO4-->
CH3 CH2 CH2C =CH2 (g)+H2O(l)
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(l).Similarities of alkanols with Hydrocarbons.
I. Similarity with alkanes.
Both alkanols and alkanes burn with a blue non-sooty
flame to form Carbon(IV) oxide, (in excess air /oxygen)
or Carbon(II)oxide (in limited air) and water.
This shows they are saturated with low C:H ratio.
e.g.Both ethanol and ethane ignite and burns in air with a
blue non-sooty flame to form Carbon(IV)oxide(in excess
air/oxygen) or Carbon(II)oxide(in limited air) and water.
CH2CH2OH(l)+3O2(g) --->2CO2(g) + 3H2O(l) (in excess air)
CH2CH2OH(l)+2O2(g)---> 2CO(g) +3H2O(l) (in limited air)
CH3CH3(g)+3O2(g) --> 2CO2(g) + 3H2O(l) (in excess air)

2CH3CH3(g) + 5O2(g)----> 4CO(g) + 6H2O(l)(in limited air)

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 II.Similarlity with Alkenes/Alkynes.
Both alkanols (R-OH) and alkenes/alkynes
(with -C = C - double and – C C- triple bond
respectively):
(i).Decolorize acidified KMnO4
(ii).Turns Orange acidified K2Cr2O7 to green.
- Alkanols(R-OH) are oxidized to alkanals (R-O) and
then to alkanoic acids (R-OOH).
- Alkenes are oxidized to alkanols with duo/double
functional groups as shown in the examples below.

[email protected] 193
Examples.
1.When ethanol is warmed with three drops of acidified
K2Cr2O7 ,the orange colour of acidified K2Cr2O7 turns to
green. Ethanol is oxidized to ethanal and then to ethanoic
acid.
Ethanol + [O] --> Ethanal , + [O] ----> Ethanoic acid.
CH3CH2OH + [O] --> CH3CH2O + [O] --->
CH3COOH.
2.When ethene is bubbled in a test tube containing
acidified K2Cr2O7 ,the orange colour of acidified K2Cr2O7
turns to green. Ethene is oxidized to ethan-1,2-diol.
Ethene + [O] -------> Ethan-1,2-diol.
H2C=CH2 + [O] --------> HOCH2 -CH2OH
[email protected] 194
III. Differences with alkenes/alkynes.
Alkanols do not decolorize bromine and chlorine
water while alkenes/alkynes decolorizes bromine and
chlorine water to form halogenoalkanols.
Example.
When ethene is bubbled into a test tube containing
bromine water, the bromine water is decolorized.
Ethene is oxidized to bromoethanol.
Ethene + Bromine water ------> Bromoethanol.
H2C=CH2 + HOBr -------> BrCH2 -CH2OH

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IV. Differences in melting and boiling point with
Hydrocarbons.
Alkanols have higher melting point than the
corresponding hydrocarbons
(ie.alkane/alkene/alkyne)
This is because most alkanols exist as dimers
NB.A dimer is a molecule made up of two other
molecules usually joined together by van-der-
waals forces/hydrogen bond or dative bonds.
Two alkanol molecules form a dimer joined by
hydrogen bonds.
[email protected] 196
Hydrogen bonds covalent bonds

R1 O δ-……….…H δ + O δ-

H δ+ R2

R1 and R2 are alkyl extensions of the

molecule.
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Example
In Ethanol the oxygen atom attracts/pulls the shared
electrons in the covalent bond more to itself than
Hydrogen.
This creates a partial negative charge (δ-) on oxygen and
partial positive charge(δ+) on hydrogen.
Two ethanol molecules attract each other at the partial
charges through Hydrogen bonding forming a dimmer.
Dimerization of alkanols means more energy is needed to
break/weaken the Hydrogen bonds .
All organic compounds require to break /weaken the
intermolecular forces attraction joining the molecules
before boiling/melting.
[email protected] 198
 An ethanol dimer from hydrogen bonding
H H
Hydrogen bond
H C C H
O

H H H H
H
O C C H

H H
Covalent bonds

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E.USES OF SOME ALKANOLS.
(a).Methanol is used:-
1.As industrial alcohol.
2.Making methylated spirit.
(b).Ethanol is used:-
1. As alcohol in alcoholic drinks e.g Beer, wines
and spirits.
2.As antiseptic to wash wounds.
3.In manufacture of vanishes, ink ,glue and paint
because it is volatile and thus easily evaporate.
4.As a fuel when blended with petrol to make
gasohol.

[email protected] 200
 Legal caution!!!
Do not encourage your
institution to be a user
consumer of pirated soft wares.
Legal action can easily be
taken against both you and the
institution at your cost!!!
[email protected] 201
C.ALKANOIC ACIDS (Carboxylic acids)
(A).INTRODUCTION.
Alkanoic acids belong to a homologous series of organic
compounds with a general formula CnH2n +1 COOH and
thus -COOH as the functional group .
Alkanoic acids like alkanols /alkanes/alkenes/alkynes
form a homologous series where:
(i).the general name of an alkanoic acids is derived from
the alkane name then ending with “–oic” acid.
(ii).the members have R-COOH/ R - C-O-H as the
functional group.

O [email protected] 202
 (iii).they have the same general formula represented
by R-COOH where R is an alkyl group.
(iv).each member differ by –CH2- group from the
next/previous.
(v).they show a similar and gradual change in their
physical properties e.g. boiling and melting point.
(vi).they show similar and gradual change in their
chemical properties.
(vii).since they are acids they show similar properties
with mineral acids
The 1st ten alkanoic acids include:

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n General Structural formula IUPAC name
/molecular
formular
0 HCOOH Methanoic
H–C–O-H acid

O
1 CH3 COOH H Ethanoic acid

H–C –C–O-H

H O
2 CH3CH2COOH H H Propanoic acid
C2H5COOH
H- C – C – C – O – H

H H O
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3 CH3 CH2 CH2 COOH H H H Butanoic
C3 H7 COOH acid
H- C- C–C –C–O–H

H H H O

4 CH3CH2CH2CH2 H H H H Pentanoic
COOH acid
C4 H9 COOH H- C–C- C–C –C–O–H

H H H H O

5 CH3CH2 CH2CH2CH2 H H H H H Hexanoic

COOH acid
C5 H11 COOH H C- C–C- C–C –C–O–H

H H H H H O

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(B) ISOMERS OF ALKANOIC ACIDS.
Alkanoic acids exhibit both structural and position
isomerism.
The isomers are named by using the following basic
guidelines
(i)Like alkanes. identify the longest carbon chain to be
the parent name.
(ii)Identify the position of the -C-O-H functional

O
group to give it the smallest /lowest position.
(iii)Identify the type and position of the side group
branches.
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Practice examples on isomers of alkanoic acids
1.Isomers of butanoic acid C3H7COOH
CH3 CH2 CH2 COOH
Butan-1-oic acid

CH3

H3C C COOH 2-methylpropan-1-oic acid

2-methylpropan-1-oic acid and Butan-1-oic acid are

structural isomers because the position of the functional
group does not change but the arrangement of the atoms
in the molecule does.
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 2.Isomers of pentanoic acid C4H9COOH

CH3CH2CH2CH2 COOH pentan-1-oic acid

CH3

CH3CH2CH COOH 2-methylbutan-1-oic acid

CH3

H3C C COOH 2,2-dimethylpropan-1-oic

acid

CH3 [email protected] 208

3.Ethan-1,2-dioic acid
O O

HOOC- COOH or H-O–C - C–O–H

4.Propan-1,3-dioic acid

O H O

HOOC-CH2 COOH or H-O–C–C-C–O–H

5.Butan-1,4-dioic acid H

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(C). LABORATORY AND INDUSTRIAL
PREPARATIONOF ALKANOIC ACIDS.
In a school laboratory, alkanoic acids can be
prepared by adding an oxidizing agent (H+/KMnO4 or
H+ / K2Cr2O7) to the corresponding alkanol then warming.
The oxidation converts the alkanol first to an alkanal the
alkanoic acid.
NB Acidified KMnO4 is a stronger oxidizing agent than
acidified K2Cr2O7
General equation:
R- CH2 – OH + [O]--H+/KMnO4--> R- CH– O + H2O(l)
(alkanol) (alkanal)
R- CH – O + [O] --H+/KMnO4--> R- C– OOH
(alkanal) (alkanoic acid)
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Examples.
1.Ethanol on warming in acidified KMnO4 is oxidized
to ethanal then ethanoic acid .
CH3-CH2– OH+[O] -H+/KMnO4-->CH3-CH– O + H2O(l)
(ethanol) (ethanal)
CH3-CH – O + [O]--H+/KMnO4--> CH3-C– OOH
(ethanal) (ethanoic acid)
2.Propanol on warming in acidified KMnO4 is oxidized
to propanal then propanoic acid
CH3CH2CH2– OH+[O]--H+/KMnO4-->
CH3CH2CH – O + H2O(l)
(propanol) (propanal)
CH3CH2CH – O + [O]--H+/KMnO4--> CH3CH2C– OOH
(propanal) (propanoic acid)
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 Industrially,large scale manufacture of alkanoic acid like
ethanoic acid is obtained from:
(a).Alkenes reacting with steam at high temperatures and
pressure in presence of phosphoric(V)acid catalyst and
undergo hydrolysis to form alkanols. i.e.
Alkenes + Steam/water -- H2PO4 Catalyst--> Alkanol
The alkanol is then oxidized by air at 5 atmosphere
pressure with Manganese (II)sulphate(VI) catalyst to form
the alkanoic acid.

Alkanol+Air--MnSO4 Catalyst/5atm pressure->alkanoic

acid
[email protected] 212
 Example
Ethene is mixed with steam over a phosphoric(V)acid
catalyst,300oC temperature and 60 atmosphere pressure to
form ethanol.
CH2=CH2 + H2O -> CH3 CH2OH
(Ethene) (Ethanol)
This is the industrial large scale method of
manufacturing ethanol
Ethanol is then oxidized by air at 5 atmosphere
pressure with Manganese (II)sulphate(VI) catalyst to form
the ethanoic acid.
CH3 CH2OH + [O]-- MnSO4 Catalyst/5 atm pressure-->
CH3 COOH
(Ethanol) [email protected](Ethanoic acid)
213
(b)Alkynes react with liquid water at high
temperatures and pressure in presence of
Mercury(II) sulphate(VI) catalyst and 30%
concentrated sulphuric(VI)acid to form alkanals.
Alkyne + Water -- Mercury(II)sulphate(VI) -->
Alkanal
The alkanal is then oxidized by air at 5 atmosphere
pressure with Manganese (II) sulphate(VI) catalyst
to form the alkanoic acid.
Alkanal + air/oxygen --
Manganese(II)sulphate(VI)catalyst-->
Alkanoic acid
[email protected] 214
Example
Ethyne react with liquid water at high temperature and pressure with
Mercury (II) sulphate (VI)catalyst and 30% concentrated
sulphuric(VI)acid to form ethanal.
CH = CH + H2O --HgSO4--> CH3 CH2O
(Ethyne) (Ethanal)

This is another industrial large scale method of

manufacturing ethanol from large quantities of ethyne
found in natural gas.
Ethanal is then oxidized by air at 5 atmosphere pressure with
Manganese (II)sulphate(VI) catalyst to form the ethanoic acid.
CH3 CH2O +[O] -- MnSO4 Catalyst/5 atm pressure--> CH3 COOH
(Ethanal) (Oxygen from air) (Ethanoic acid)
[email protected] 215
(D) PHYSICAL AND CHEMICAL PROPERTIES OF
ALKANOIC ACIDS.
I.Physical properties of alkanoic acids
The table below shows some physical properties of
alkanoic acids
Alkanol Melting Boiling Density Solubility in
point(oC) point(oC) (gcm-3) water
Methanoic 18.4 101 1.22 soluble
acid
Ethanoic 16.6 118 1.05 soluble
acid
Propanoic -2.8 141 0.992 soluble
acid
Butanoic -8.0 164 0.964 soluble
acid [email protected] 216
Pentanoic -9.0 187 0.939 Slightly
acid soluble
Hexanoic -11 205 0.927 Slightly
acid soluble
Heptanoic -3 223 0.920 Slightly
acid soluble
Octanoic 11 239 0.910 Slightly
acid soluble
Nonanoic 16 253 0.907 Slightly
acid soluble
Decanoic 31 269 0.905 Slightly
acid soluble

From the table note the following:

[email protected] 217
•Melting and boiling point decrease as the carbon chain
increases due to increase in intermolecular forces of
attraction between the molecules requiring more energy to
separate the molecules.
•The density decreases as the carbon chain increases as
the intermolecular forces of attraction increases between
the molecules making the molecule very close reducing
their volume in unit mass.
•Solubility decreases as the carbon chain increases as the
soluble –COOH end is shielded by increasing insoluble
alkyl/hydrocarbon chain.
Like alkanols ,alkanoic acids exist as dimmers due to the
hydrogen bonds within the molecule. i.e..
[email protected] 218
 Hydrogen bonds covalent bonds

R1 C O δ-…….….…H δ+ O δ-

O δ- H δ+……..….O δ- C R2

R1 and 2 are extensions of the molecule.

For ethanoic acid the extension is made up of
CH3 – to make the structure; [email protected] 219
For ethanoic acid the extension is made up of
CH3 – to make the structure;
Hydrogen bonds covalent bonds

CH3 C O δ-…………… H δ+ O δ-

O δ- H δ+…………O δ- C CH3
Ethanoic acid has a higher melting/boiling point than
ethanol .This is because ethanoic acid has two/more
hydrogen bond than ethanol. [email protected] 220
II Chemical properties of alkanoic acids
The following experiments shows the main
chemical properties of ethanoic(alkanoic) acid.
(a)Effect on litmus papers
Experiment
Dip both blue and red litmus papers in ethanoic
acid. Repeat with a solution of succinic acid, citric
acid, oxalic acid, tartaric acid and dilute
nitric(V)acid.
Sample observations

[email protected] 221
Solution/acid Observations/effect on litmus papers Inference
Ethanoic acid Blue litmus paper turn red H3O+/H+(aq)ion
Red litmus paper remain red
Succinic acid Blue litmus paper turn red H3O+/H+(aq)ion
Red litmus paper remain red
Citric acid Blue litmus paper turn red H3O+/H+(aq)ion
Red litmus paper remain red
Oxalic acid Blue litmus paper turn red H3O+/H+(aq)ion
Red litmus paper remain red
Tartaric acid Blue litmus paper turn red H3O+/H+(aq)ion
Red litmus paper remain red
Nitric(V)acid Blue litmus paper turn red H3O+/H+(aq)ion
Red litmus paper remain red
Explanation
All acidic solutions contains H+/H3O+(aq) ions.
The H+ /H3O+ (aq) ions is responsible for turning blue
litmus paper/solution to red [email protected] 222
 (b)pH
Experiment
Place 2cm3 of ethanoic acid in a test tube. Add 2 drops of universal
indicator solution and determine its pH.
Repeat with a solution of succinic acid, citric acid, oxalic acid,
tartaric acid and dilute sulphuric (VI)acid.
Sample observations
Solution/acid pH Inference
Ethanoic acid 4/5/6 Weakly acidic
Succinic acid 4/5/6 Weakly acidic
Citric acid 4/5/6 Weakly acidic
Oxalic acid 4/5/6 Weakly acidic
Tartaric acid 4/5/6 Weakly acidic
Sulphuric(VI)acid 1/2/3 Strongly acidic
[email protected] 223
Explanations
Alkanoic acids are weak acids that partially/partly
dissociate to release few H+ ions in solution.
The pH of their solution is thus 4/5/6 showing they form
weakly acidic solutions when dissolved in water.
All alkanoic acid dissociate to releases the “H” at the
functional group in -COOH to form the alkanoate ion; –
COO-
Mineral acids(Sulphuric(VI)acid, Nitric(V)acid and
Hydrochloric acid) are strong acids that wholly/fully
dissociate to release many H+ ions in solution.
The pH of their solution is thus 1/2/3 showing they form
strongly acidic solutions when dissolved in water.i.e
Examples [email protected] 224
CH3COOH(aq) CH3COO-(aq) + H+(aq)
(ethanoic acid) (ethanoate ion) (few H+ ion)

CH3 CH2COOH(aq) CH3 CH2COO-(aq) + H+(aq)

(propanoic acid) (propanoate ion) (few H+ ion)

HOOH(aq) HOO-(aq) + H+(aq)

(methanoic acid) (methanoate ion) (few H+ ion)

H2 SO4 (aq) SO42- (aq) + 2H+(aq)

(sulphuric(VI) acid) (sulphate(VI) ion) (many H+ ion)

HNO3 (aq) NO3- (aq) + H+(aq)

(nitric(V) acid) (nitrate(V) ion) (many H+ ion)
[email protected] 225
(c)Reaction with metals
Experiment
Place about 4cm3 of ethanoic acid in a test tube.
Put about 1cm length of polished magnesium
ribbon.
Test any gas produced using a burning splint.
Repeat with a solution of succinic acid, citric
acid, oxalic acid, tartaric acid and dilute sulphuric
(VI) acid.
Sample observations
[email protected] 226
Solution/acid Observations Inference
Ethanoic acid (i)effervescence, fizzing, bubbles H3O+/H+(aq)ion
(ii)colourless gas produced that burn
with “pop” sound/explosion
Succinic acid (i)effervescence, fizzing, bubbles H3O+/H+(aq)ion
(ii)colourless gas produced that burn
with “pop” sound/explosion
Citric acid (i)effervescence, fizzing, bubbles H3O+/H+(aq)ion
(ii)colourless gas produced that burn
with “pop” sound/explosion
Oxalic acid (i)effervescence, fizzing, bubbles H3O+/H+(aq)ion
(ii)colourless gas produced that burn
with “pop” sound/explosion
Tartaric acid (i)effervescence, fizzing, bubbles H3O+/H+(aq)ion
(ii)colourless gas produced that burn
with “pop” sound/explosion
Nitric(V)acid (i)effervescence, fizzing, bubbles H3O+/H+(aq)ion
(ii)colourless gas produced that burn
with “pop” sound/explosion [email protected] 227
Explanation
Metals higher in the reactivity series displace the
hydrogen in all acids to evolve/produce hydrogen gas
and form a salt.
Alkanoic acids react with metals with metals to form
alkanoates salt and produce/evolve hydrogen gas.
.Hydrogen extinguishes a burning splint with a pop
sound/explosion.
Only the “H”in the functional group -COOH is /are
displaced and not in the alkyl hydrocarbon chain.

Alkanoic acid + Metal -> Alkanoate + Hydrogen

gas. i.e.
[email protected] 228
Examples
1. For a monovalent metal with monobasic acid
2R – COOH + 2M -> 2R- COOM + 2H2(g)

2.For a divalent metal with monobasic acid

2R – COOH + M -> (R- COO) 2M + H2(g)

3.For a divalent metal with dibasic acid

HOOC-R-COOH+ M -> MOOC-R-COOM + H2(g)

4.For a monovalent metal with dibasic acid

HOOC-R-COOH+ 2M -> MOOC-R-COOM + H2(g)

[email protected] 229
5 (i)Sulphuric(VI)acid is a dibasic acid
H2 SO4 (aq) + 2M -> M2 SO4 (aq) + H2(g)
H2 SO4 (aq) + M -> MSO4 (aq) + H2(g)

(ii)Nitric(V) is a monobasic acid

2HNO3 (aq) + 2M -> 2MNO3 (aq) + H2(g)
2HNO3 (aq) + M -> M(NO3 ) 2 (aq) + H2(g)
(iii)hydrochloric acid is a monobasic acid
2HCl (aq) + 2M -> 2MCl (aq) + H2(g)
2HCl (aq) + M -> MCl 2 (aq) + H2(g)

[email protected] 230
Examples
1.Sodium reacts with ethanoic acid to form sodium
ethanoate and produce hydrogen gas.
Caution: This reaction is explosive.
2CH3COOH (aq)+ 2Na(s) -> 2CH3COONa (aq) + H2(g)
(Ethanoic acid) (Sodium ethanoate)
2.Calcium reacts with ethanoic acid to form calcium
ethanoate and produce hydrogen gas.
2CH3COOH (aq)+ Ca(s) ->(CH3COO) 2Ca (aq) + H2(g)
(Ethanoic acid) (Calcium ethanoate)
3.Sodium reacts with ethan-1,2-dioic acid to form sodium
ethan-1,2-dioate and produce hydrogen gas.
HOOC-R-COOH+ 2Na -> NaOOC - COONa + H2(g)
(ethan-1,2-dioic acid) (sodium ethan-1,2-dioate)
[email protected] 231
Commercial name of ethan-1,2-dioic acid is oxalic acid.
The salt is sodium oxalate.

4.Magnesium reacts with ethan-1,2-dioic acid to form

magnesium ethan-1,2-dioate and produce. hydrogen gas.
HOOC-R-COOH+ Mg -> ( OOC - COO) Mg + H2(g)
(ethan-1,2-dioic acid) (magnesium ethan-1,2-dioate)
5.Magnesium reacts with
(i)Sulphuric(VI)acid to form Magnesium sulphate(VI)
H2 SO4 (aq) + Mg -> MgSO4 (aq) + H2(g)
(ii)Nitric(V) and hydrochloric acid are monobasic acid
2HNO3 (aq) + Mg -> M(NO3 ) 2 (aq) + H2(g)

[email protected] 232
(d)Reaction with hydrogen carbonates and carbonates
Experiment
Place about 3cm3 of ethanoic acid in a test tube.
Add about 0.5g/ ½ spatula end full of sodium
hydrogen carbonate/sodium carbonate.
Test the gas produced using lime water.
Repeat with a solution of succinic acid, citric
acid, oxalic acid, tartaric acid and dilute sulphuric
(VI) acid.

Sample observations
[email protected] 233
Solution/acid Observations Inference
Ethanoic acid (i)effervescence, fizzing, bubbles H3O+/H+(aq)ion
(ii)colourless gas produced that forms
a white precipitate with lime water
Succinic acid (i)effervescence, fizzing, bubbles H3O+/H+(aq)ion
(ii)colourless gas produced that forms
a white precipitate with lime water
Citric acid (i)effervescence, fizzing, bubbles H3O+/H+(aq)ion
(ii)colourless gas produced that forms
a white precipitate with lime water
Oxalic acid (i)effervescence, fizzing, bubbles H3O+/H+(aq)ion
(ii)colourless gas produced that forms
a white precipitate with lime water
Tartaric acid (i)effervescence, fizzing, bubbles H3O+/H+(aq)ion
(ii)colourless gas produced that forms
a white precipitate with lime water
Nitric(V)acid (i)effervescence, fizzing, bubbles H3O+/H+(aq)ion
(ii)colourless gas produced that forms
a white precipitate with lime water
[email protected] 234
All acids react with hydrogen carbonate/carbonate to form
salt ,water and evolve/produce bubbles of carbon(IV)
oxide and water.
Carbon(IV)oxide forms a white precipitate when bubbled
in lime water/extinguishes a burning splint.
Alkanoic acids react with hydrogen carbonate/carbonate
to form alkanoates ,water and evolve/produce bubbles of
carbon(IV)oxide and water.
Alkanoic acid + hydrogen carbonate -> alkanoate + water
+ carbon(IV)oxide
Alkanoic acid + carbonate -> alkanoate + water
+ carbon(IV)oxide
Examples
[email protected] 235
1.Sodium hydrogen carbonate reacts with ethanoic acid to form
sodium ethanoate ,water and carbon(IV)oxide gas.
CH3COOH (aq)+NaHCO3 (s) ->CH3COONa(aq)+H2O(l)+CO2 (g)
(Ethanoic acid) (Sodium ethanoate)
2.Sodium carbonate reacts with ethanoic acid to form sodium
ethanoate ,water and carbon(IV)oxide gas.
2CH3COOH (aq)+Na2CO3(s)->2CH3COONa(aq)+H2O(l)+CO2 (g)
(Ethanoic acid) (Sodium ethanoate)
3.Sodium carbonate reacts with ethan-1,2-dioic acid to form sodium
ethanoate ,water and carbon(IV)oxide gas.
HOOC-COOH+Na2CO3(s)->NaOOC - COONa +H2O(l)+CO2 (g)
(ethan-1,2-dioic acid) (sodium ethan-1,2-dioate)
4.Sodium hydrogen carbonate reacts with ethan-1,2-dioic acid to
form sodium ethanoate ,water and carbon(IV)oxide gas.
HOOC-COOH+2NaHCO3(s)->NaOOC-COONa+H2O(l)+2CO2 (g)
(ethan-1,2-dioic acid) (sodium ethan-1,2-dioate)
[email protected] 236
(e)Esterification
Experiment
Place 4cm3 of ethanol in a boiling tube.
Add equal volume of ethanoic acid.
To the mixture, add 2 drops of concentrated
sulphuric(VI)acid carefully.
Warm/heat gently on Bunsen flame.
Pour the mixture into a beaker containing 50cm3 of
water.
Smell the products.
Repeat with a solution of succinic acid, citric acid, oxalic
acid, tartaric acid and dilute sulphuric (VI) acid.
Sample observations
[email protected] 237
Solution/acid Observations
Ethanoic acid Sweet fruity smell
Succinic acid Sweet fruity smell
Citric acid Sweet fruity smell
Oxalic acid Sweet fruity smell
Tartaric acid Sweet fruity smell
Dilute No sweet fruity smell
sulphuric(VI)acid

Explanation
Alkanols react with alkanoic acid to form the sweet smelling
homologous series of esters and water.
The reaction is catalysed by concentrated sulphuric(VI)acid in the
laboratory but naturally by sunlight /heat.
Each ester has a characteristic smell derived from the many
possible combinations of alkanols and [email protected]
acids. 238
Alkanol + Alkanoic acids -> Ester + water
Esters derive their names from the alkanol first then
alkanoic acids. The alkanol “becomes” an alkyl group
and the alkanoic acid “becomes” alkanoate hence
alkylalkanoate. e.g.
Ethanol + Ethanoic acid -> Ethylethanoate + Water
Ethanol + Propanoic acid -> Ethylpropanoate + Water
Ethanol + Methanoic acid -> Ethylmethanoate + Water
Ethanol + butanoic acid -> Ethylbutanoate + Water
Propanol + Ethanoic acid->Propylethanoate + Water
Methanol+Ethanoic acid->Methyethanoate + Water
Methanol+Decanoic acid->Methyldecanoate + Water
Decanol +Methanoic acid->Decylmethanoate + Water
[email protected] 239
During the formation of the ester, the “O” joining the
alkanol and alkanoic acid comes from the alkanol.
R1 -COOH + R2 –OH -> R1 -COO –R2 + H2O
Examples
1. Ethanol reacts with ethanoic acid to form the ester
ethyl ethanoate and water.
Ethanol + Ethanoic acid --Conc. H2SO4 -->
Ethylethanoate + Water
C2H5OH (l) + CH3COOH(l) --Conc. H2SO4 -->
CH3COO C2H5(aq) +H2O(l)
CH3CH2OH (l)+ CH3COOH(l) --Conc. H2SO4 -->
CH3COOCH2CH3(aq) +H2O(l)

[email protected] 240
 Legal caution!!!
Do not encourage your
institution to be a user
consumer of pirated soft wares.
Legal action can easily be
taken against both you and the
institution at your cost!!!
[email protected] 241
C. DETERGENTS

Detergents are cleaning agents that improve the

cleaning power /properties of water.
A detergent therefore should be able to:
(i)dissolve substances which water can not
e.g grease ,oil, fat
(ii)be washed away after cleaning.
There are two types of detergents:
(a)Soapy detergents
(b)Soapless detergents
[email protected] 242
•SOAPY DETERGENTS
Soapy detergents usually called soap is long chain salt of
organic /alkanoic acids.
Common soap is sodium octadecanoate .
It is derived from reacting concentrated sodium hydroxide
solution with octadecanoic acid(18 carbon alkanoic acid)
Sodium hydroxide + octadecanoic acid ->
Sodium octadecanoate + water
NaOH(aq) + CH3 (CH2) 16 COOH(aq) ->
CH3 (CH2) 16 COO – Na+ (aq) +H2 O(l)
Commonly ,soap can thus be represented ;
R- COO – Na+ where;
R is a long chain alkyl group and -COO – Na+ is the
alkanoate ion. [email protected] 243
In a school laboratory and at industrial and domestic
level,soap is made by reacting concentrated sodium
hydroxide solution with esters from (animal) fat and oil.
The process of making soap is called saponification.
During saponification ,the ester is hydrolyzed by the
alkali to form sodium salt /soap and glycerol /propan-
1,2,3-triol is produced.
Fat/oil(ester)+sodium/potassium hydroxide->
sodium /potassium salt(soap)+ glycerol
Fats/Oils are esters with fatty acids and glycerol parts in
their structure;

[email protected] 244
 Structure of Fat/oil

C17H35COOCH2

C17H35COOCH

C17H35COOCH2

Fatty acid part Glycerol part

[email protected] 245
When boiled with concentrated sodium hydroxide
solution NaOH;
(i) NaOH ionizes/dissociates into Na+ and OH-
ions
(ii)fat/oil split into three C17H35COO- and one
CH2 CH CH2
(iii) the three Na+ combine with the three
C17H35COO- to form the salt C17H35COO- Na+
(iv)the three OH-ions combine with the CH2 CH
CH2 to form an alkanol with three functional
groups CH2 OH CH OH CH2 OH(propan-1,2,3-
triol) [email protected] 246
C17H35COOCH2 CH2OH

C17H35COOCH + NaOH -> 3 C17H35COO- Na+ + CHOH

C17H35COOCH2 CH2OH
Ester Alkali Soap glycerol

Generally:
CnH2n+1COOCH2 CH2OH

CnH2n+1COOCH + NaOH -> 3 CnH2n+1COO- Na+ + CHOH

CnH2n+1COOCH2 CH2OH
Ester Alkali Soap glycerol

[email protected] 247
R - COOCH2 CH2OH

R - COOCH +NaOH -> 3R-COO- Na+ + CHOH

R- COOCH2 CH2OH
Ester Alkali Soap glycerol

During this process a little sodium chloride is added to

precipitate the soap by reducing its solubility.
This is called salting out.
The soap is then added colouring agents ,perfumes and
herbs of choice.
[email protected] 248
School laboratory preparation of soap
Place about 40 g of fatty (animal fat)beef/meat in 100cm3
beaker .
Add about 15cm3 of 4.0M sodium hydroxide solution.
Boil the mixture for about 15minutes.
Stir the mixture .
Add about 5.0cm3 of distilled water as you boil to make
up for evaporation.
Boil for about another 15minutes.Add about four spatula
end full of pure sodium chloride crystals. Continue
stirring for another five minutes. Allow to cool.
Filter of /decant and wash off the residue with distilled
water .
Transfer the clean residue into a dry beaker. Preserve.
[email protected] 249
The action of soap
Soapy detergents:
(i)act by reducing the surface tension of water by
forming a thin layer on top of the water.
(ii)is made of a non-polar alkyl /hydrocarbon tail
and a polar -COO-Na+ head.
The non-polar alkyl /hydrocarbon tail is hydrophobic
(water hating) and thus does not dissolve in water .It
dissolves in non-polar solvent like grease, oil and fat.
The polar -COO-Na+ head is hydrophilic (water
loving)and thus dissolve in water.
When washing with soapy detergent, the non-polar tail of
the soapy detergent surround/dissolve in the dirt on the
garment /grease/oil while the polar head dissolve in
water. [email protected] 250
Through mechanical agitation /stirring /squeezing/
rubbing/ beating/kneading, some grease is dislodged
/lifted of the surface of the garment.
It is immediately surrounded by more soap molecules
It float and spread in the water as tiny droplets that
scatter light in form of emulsion making the water
cloudy and shinny.
It is removed from the garment by rinsing with fresh
water.
The repulsion of the soap head prevent /ensure the
droplets do not mix.
Once removed, the dirt molecules cannot be redeposited
back because it is surrounded by soap molecules.
[email protected] 251
Advantages and disadvantages of using soapy
detergents
Soapy detergents are biodegradable. They are acted upon
by bacteria and rot. They thus do not cause environmental
pollution.
Soapy detergents have the following disadvantage:
(i)forms an insoluble precipitate with hard water
called scum.
Scum is insoluble calcium octadecanoate and Magnesium
octadecanoate formed when soap reacts with Ca2+ and
Mg2+ present in hard water.
Chemical equation
[email protected] 252
2C17H35COO- Na+ (aq) + Ca2+(aq) ->
(C17H35COO- )2Ca2+ (s) + 2Na+(aq)
(insoluble Calcium octadecanote/scum)

2C17H35COO- Na+ (aq) + Mg2+(aq) ->

(C17H35COO- )2Mg2+ (s) + 2Na+(aq)
(insoluble Magnesium octadecanote/scum)

This causes wastage of soap.

Potassium soaps are better than Sodium soap.

Potassium is more expensive than sodium and thus its
soap is also more expensive.
[email protected] 253
 (b)SOAPLESS DETERGENTS
Soapless detergent usually called detergent is a long
chain salt formed from by-products of fractional
distillation of crude oil.
Commonly used soaps include:
(i)washing agents
(ii)toothpaste
(iii)emulsifiers/wetting agents/shampoo
Soapless detergents are derived from reacting:
(i)concentrated sulphuric(VI)acid with a long chain
alkanol e.g. Octadecanol(18 carbon alkanol) to form alkyl
hydrogen sulphate(VI)
Alkanol + Conc sulphuric(VI)acid ->
alkyl hydrogen sulphate(VI) + Water
[email protected] 254
R –OH + H2SO4 -> R –O-SO3H + H2O
(ii)the alkyl hydrogen sulphate(VI) is then neutralized
with sodium/potassium hydroxide to form sodium /
potassium alkyl hydrogen sulphate(VI)
Sodium/potassium alkyl hydrogen sulphate(VI) is the
soapless detergent.

alkyl hydrogen + Potassium/sodium ->

sulphate(VI) hydroxide
Sodium/potassium + Water
alkyl hydrogen sulphate(VI)
R –O-SO3H + NaOH -> R –O-SO3- Na+ + H2O
[email protected] 255
Example
Step I : Reaction of Octadecanol with Conc.H2SO4
C17H35CH2OH (aq) + H2SO4 ->
C17H35CH2-O- SO3- H+ (aq) + H2O (l)
octadecanol + sulphuric(VI)acid ->
Octadecyl hydrogen sulphate(VI) + water
Step II: Neutralization by an alkali
C17H35CH2-O- SO3- H+ (aq) + NaOH ->
C17H35CH2-O- SO3- Na+ (aq) + H2O (l)
Octadecyl hydrogen + sodium/potassium ->
sulphate(VI) hydroxide
sodium/potassium octadecyl +Water
[email protected] 256

hydrogen sulphate(VI)
School laboratory preparation of soapless
detergent
Place about 20g of olive oil in a 100cm3 beaker.
Put it in a trough containing ice cold water.
Add dropwise carefully 18M concentrated
sulphuric(VI)acid stirring continuously into the
olive oil until the oil turns brown.
Add 30cm3 of 6M sodium hydroxide
solution.Stir.
This is a soapless detergent.

[email protected] 257
The action of soapless detergents

The action of soapless detergents is similar to that of

soapy detergents.
The soapless detergents contain the hydrophilic head and
a long hydrophobic tail. i.e.

vvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvv-COO-Na+

vvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvvv -O-SO3- Na+

(long hydrophobic / ( polar/ionic head
non-polar alkyl tail) hydrophilic)

[email protected] 258
The tail dissolves in fat/grease/oil while the
ionic/polar/ionic head dissolves in water.
The tail stick to the dirt which is removed by the
attraction of water molecules and the polar /ionic
/hydrophilic head by mechanical agitation /squeezing
/kneading / beating/rubbing/scrubbing/ scatching.
The suspended dirt is then surrounded by detergent
molecules and repulsion of the anion head preventing the
dirt from sticking on the material garment.
The tiny droplets of dirt emulsion makes the water
cloudy.
On rinsing the cloudy emulsion is washed away.
[email protected] 259
 Advantages and disadvantages of using soapless
detergents
Soapless detergents are non-biodegradable unlike
soapy detergents.
They persist in water during sewage treatment by
causing foaming in rivers ,lakes and streams leading to
marine /aquatic death.
Soapless detergents have the advantage in that they:
(i)do not form scum with hard water.
(ii)are cheap to manufacture/buying
(iii)are made from petroleum products but soap is
made from fats/oil for human consumption.

[email protected] 260
Sample revision questions
1. Study the scheme below
KOH
Fat /oil

Boiling Sodium Chloride

Filtration

Residue X Filtrate Y
[email protected] 261
(a)Identify the process
Saponification

(b)Fats and oils are esters. Write the formula of the a

common structure of ester
C17H35COOCH2

C17H35COOCH

C17H35COOCH2

(c)Write a balanced equation for the reaction taking

place during boiling
[email protected] 262
C17H35COOCH2 CH2OH

C17H35COOCH +3NaOH->3 C17H35COO- Na+ + CHOH

C17H35COOCH2 CH2OH
(d)Give the IUPAC name of:
(i)Residue X
Potassium octadecanoate
(ii)Filtrate Y
Propan-1,2,3-triol
(e)Give one use of fitrate Y
Making paint
(f)What is the function of sodium chloride
To reduce the solubility of the soap hence helping in precipitating it
out [email protected] 263
(g)Explain how residue X helps in washing.
Has a non-polar hydrophobic tail that dissolves in
dirt/grease /oil/fat
Has a polar /ionic hydrophilic head that dissolves in
water.
From mechanical agitation,the dirt is plucked out of the
garment and surrounded by the tail end preventing it
from being deposited back on the garment.

(h)State one:
(i)advantage of continued use of residue X on the
environment
Is biodegradable and thus do not pollute the environment
[email protected] 264
(ii)disadvantage of using residue X
Uses fat/oil during preparation/manufacture which are
better used for human consumption.
(i)Residue X was added dropwise to some water.The
number of drops used before lather forms is as in the
table below.
Water sample

A B C
Drops of residue X 15 2 15
Drops of residue X in boiled water 2 2 15
(i)State and explain which sample of water is:
I. Soft [email protected] 265
Sample B .
Very little soap is used and no effect on amount of soap
even on boiling/heating.
II. Permanent hard
Sample C .
A lot of soap is used and no effect on amount of soap
even on boiling/heating.
Boiling does not remove permanent hardness of water.
III. Temporary hard
Sample A .
A lot of soap is used before boiling. Very little soap is
used on boiling/heating.
Boiling remove temporary hardness of water.
[email protected] 266
(ii)Write the equation for the reaction at water
sample C.
Chemical equation
2C17H35COO- K+ (aq) + CaSO4(aq) ->
(C17H35COO- )Ca2+ (s) + K2SO4(aq)
Ionic equation
2C17H35COO- K+ (aq) + Ca2+(aq) ->
(C17H35COO- )Ca2+ (s) + 2K+(aq)

Chemical equation
2C17H35COO- K+ (aq) + MgSO4(aq) ->
(C17H35COO- )Mg2+ (s) + K2SO4(aq)
Ionic equation
2C17H35COO- K+ (aq) + Mg2+(aq) ->
(C17H35COO- )Mg2+ (s) + 2K+(aq)
[email protected] 267
(iii)Write the equation for the reaction at water
sample A before boiling.
Chemical equation
2C17H35COO- K+ (aq) + Ca(HCO3)(aq) ->
(C17H35COO- )Ca2+ (s) + 2KHCO3 (aq)
Ionic equation
2C17H35COO- K+ (aq) + Ca2+(aq) ->
(C17H35COO- )Ca2+ (s) + 2K+(aq)

Chemical equation
2C17H35COO- K+ (aq) + Mg(HCO3)(aq) ->
(C17H35COO- )Mg2+ (s) + 2KHCO3 (aq)
Ionic equation
2C17H35COO- K+ (aq) + Mg2+(aq) ->
(C17H35COO- )Mg2+ (s) + 2K+(aq)
[email protected] 268
(iv)Explain how water becomes hard
Natural or rain water flowing /passing through rocks
containing calcium (chalk, gypsum, limestone)and
magnesium compounds (dolomite)dissolve them to
form soluble Ca2+ and Mg2+ ions that causes water
hardness.
(v)State two useful benefits of hard water
-Used in bone and teeth formation
-Coral polyps use hard water to form coral reefs
-Snails use hard water to make their shells

2.Study the scheme below and use it to answer the

questions that follow.
[email protected] 269
Olive oil Conc. H2SO4

Ice cold water

6M sodium
Brown solid A
hydroxide

Substance B

[email protected] 270
(a)Identify :
(i)brown solid A
Alkyl hydrogen sulphate(VI)
(ii)substance B
Sodium alkyl hydrogen sulphate(VI)
(b)Write a general formula of:
(i)Substance A.
O

R-O-S O3 H // R- O - S - O - H

O
(ii)Substance B
[email protected] 271
 O

R-O-S O3 - Na+ //
R- O - S - O - Na+

O
(c)State one
(i) advantage of continued use of substance B
-Does not form scum with hard water
-Is cheap to make
-Does not use food for human as a raw material.

(ii)disadvantage of continued use of substance B.

Is non-biodegradable therefore pollute the
environment [email protected] 272
(d)Explain the action of B during washing.
Has a non-polar hydrocarbon long tail that dissolves in dirt
/ grease /oil/fat.
Has a polar/ionic hydrophilic head that dissolves in water
Through mechanical agitation the dirt is plucked /removed
from the garment and surrounded by the tail end
preventing it from being deposited back on the garment.
(e) Ethene was substituted for olive oil in the above
process. Write the equation and name of the new
products A and B.
Product A
Ethene + Sulphuric(VI)acid ->Ethyl hydrogensulphate(VI)
H2C=CH2 +H2SO4 –> H3C – CH2 –O-SO3H
[email protected] 273
Product B
Ethyl hydrogen sulphate(VI) + sodium hydroxide ->
sodium Ethyl + Water
hydrogen sulphate(VI)
H3C – CH2 –O-SO3H + NaOH ->
H3C – CH2 –O-SO3-Na+ + H2O

(f)Ethanol can also undergo similar reactions forming new

products A and B.Show this using a chemical equation.
Product A
Ethanol + Sulphuric(VI)acid ->
Ethyl hydrogen sulphate(VI) + water
H3C-CH2OH +H2SO4 –> H3C – CH2 –O-SO3H + H2O
[email protected] 274
Product B
Ethyl hydrogen sulphate(VI) + sodium hydroxide ->
sodium Ethyl + Water
hydrogen sulphate(VI)
H3C – CH2 –O-SO3H +NaOH->H3C – CH2 –O-SO3-Na+ + H2O
3.Below is part of a detergent
H3C – (CH2 )16 – O - SO3 - K +
(a)Write the formular of the polar and non-polar end
Polar end H3C – (CH2 )16 –
Non-polar end – O - SO3 - K +
(b)Is the molecule a soapy or soapless detergent?
Soapless detergent
(c)State one advantage of using the above detergent
-does not form scum with hard water
-is cheap to manufacture [email protected] 275
 Legal caution!!!
Do not encourage your
institution to be a user consumer
of pirated soft wares.
Legal action can easily be taken
against both you and the
institution at your cost!!!
[email protected] 276
 D. POLYMERS AND FIBRES
Polymers and fibres are giant molecules of organic
compounds.
Polymers and fibres are formed when small
molecules called monomers join together to form large
molecules called polymers at high temperatures and
pressures.
This process is called polymerization.
Polymers and fibres are either:
(a)Natural polymers and fibres
(b)Synthetic polymers and fibres
Natural polymers and fibres are found in living
things(plants and animals)
[email protected] 277
Natural polymers/fibres include:
-proteins/polypeptides making amino acids in animals
-cellulose that make cotton, wool,paper and silk
-Starch that come from glucose
-Fats and oils
-Rubber from latex in rubber trees
Synthetic polymers and fibres are man-made.
They include:
-polyethene
-polychloroethene(polyvinylchloride)
-polyphenylethene(polystyrene)
-Terylene(Dacron)
-Nylon-6,6
-Perspex(artificial glass) [email protected] 278
Synthetic polymers and fibres have the following
characteristic advantages over natural polymers
1. They are light and portable
2. They are easy to manufacture.
3. They can easily be molded into shape of choice.
4. They are resistant to corrosion, water, air , acids, bases
and salts.
5. They are comparatively cheap, affordable, colourful
and aesthetic
Synthetic polymers and fibres however have the
following disadvantages over natural polymers
They are non-biodegradable and hence cause
environmental pollution during disposal
[email protected] 279
•They give out highly poisonous gases when burnt like
chlorine/carbon(II)oxide
•Some on burning produce Carbon(IV)oxide. Carbon
(IV)oxide is a green house gas that cause global warming.
•Compared to some metals, they are poor conductors of
heat, electricity and have lower tensile strength.
•Safe methods of disposal
1.Recycling: Once produced all synthetic polymers/ fibres
should be recycled to a new product. This prevents
accumulation of the synthetic polymers/ fibres in the
environment.
2.Production of biodegradable synthetic polymers and
fibres that rot away.
[email protected] 280
There are two types of polymerization:
(a)addition polymerization
(b)condensation polymerization
(a)addition polymerization
Addition polymerization is the process where a small
unsaturated monomer (alkene ) molecule join together to
form a large saturated molecule.

Only alkenes undergo addition polymerization.

Addition polymers are named from the alkene/monomer
making the polymer and adding the prefix “poly” before
the name of monomer to form a polyalkene
[email protected] 281
During addition polymerization
(i)the double bond in alkenes break
(ii)free radicals are formed
(iii)the free radicals collide with each other and join to
form a larger molecule.
The more collisions the larger the molecule.
Examples of addition polymerization
1.Formation of Polyethene
Polyethene is an addition polymer formed when ethene
molecule/monomer join together to form a large
molecule/polymer at high temperatures and pressure.
During polymerization:
(i)many molecules are brought nearer to each other by the
high pressure(reduce distance between reacting paticles)
[email protected] 282
 H H H H H H H H

C=C + C=C + C=C + C= C + …

H H H H H H H H
Ethene +Ethene+ Ethene+ Ethene + …
(ii)the double bond joining the ethane molecule break
to free radicals
H H H H H H H H

• C - C • + • C - C • + • C - C • + • C - C• + …

H H H H H H H H
Free ethene radical … [email protected] 283
 (iii)the free radicals collide with each other and join to
form a larger molecule

H H H H H H H H lone pair of electrons

• C – C - C – C - C – C - C - C• + …
H H H H H H H H
Lone pair of electrons can be used to join more
monomers to form longer polyethene.
Polyethene molecule can be represented as:
H H H H H H H H extension of
polymer
- C–C - C – C - C – C - C – C -
H H H H H H H H
[email protected] 284
Since the molecule is a repetition of one monomer, then the
polymer is:
H H

(C–C )n

H H
Where n is the number of monomers in the polymer.
The number of monomers in the polymer can be determined
from the molar mass of the polymer and monomer from the
relationship:
Number of monomers/repeating units in monomer
= Molar mass polymer
Molar mass monomer [email protected] 285
Examples
Polythene has a molar mass of 4760.Calculate the
number of ethene molecules in the polymer(C=12.0,
H=1.0 )
Number of monomers/repeating units in polymer
= Molar mass polymer =>Molar mass polyethene = 4760
Molar mass monomer Molar mass ethene (C2H4 )= 28
Substituting 4760 = 170 ethene molecules
28
The commercial name of polyethene is polythene. It is an
elastic, tough, transparent and durable plastic. Polythene
is used: (i)in making plastic bag
(ii)bowls and plastic Plates
(iii)packaging [email protected] 286
2.Formation of Polychlorethene
Polychloroethene is an addition polymer formed
when chloroethene molecule/monomer join
together to form a large molecule/polymer at high
temperatures and pressure.

During polymerization:
(i)many molecules are brought nearer to each
other by the high pressure(which reduces the
volume occupied by reacting particles)

[email protected] 287
 H Cl H Cl H Cl H Cl

C=C + C=C + C=C + C= C + …

H H H H H H H H
chlorothene+ chlorothene +chlorothene + chlorothene
(ii)the double bond joining the chloroethene molecule
break to free radicals
H Cl H Cl H Cl H Cl

• C - C • + • C - C • + • C - C • + • C - C• + …

H H H H H H H H
Free chloroethene radical …[email protected] 288
 H Cl H Cl H Cl H Cl extension
of
-C-C - C -C - C -C - C - C –molecule/
polymer
H H H H H H H H
Since the molecule is a repetition of one
monomer, then the polymer is:
H H

(C–C ) n

H Cl
[email protected] 289
Examples
Polychlorothene has a molar mass of 4760.Calculate the number
of chlorethene molecules in the polymer(C=12.0, H=1.0,Cl=35.5

Number of monomers/repeating units in monomer =

Molar mass polymer
Molar mass monomer
ÞMolar mass chloroethene (C2H3Cl )= 62.5
ÞMolar mass polychloroethene = 4760
Substituting4760 = 77.16
62.5
The commercial name of polychloroethene is
polyvinylchloride(PVC).
It is a tough, non-transparent and durable plastic. PVC is used:
(i)in making plastic rope
(ii)water pipes
(iii)crates and boxes [email protected] 290
3.Formation of Polyphenylethene

Polyphenylethene is an addition polymer formed when

phenylethene molecule/monomer join together to form a
large molecule/polymer at high temperatures and
pressure.
During polymerization:
(i)many molecules are brought nearer to each other by the
high pressure(which reduces the volume occupied by
reacting particles)

[email protected] 291
 H C6H5 H C6H5 H C6H5 H C6H5

C=C + C=C + C=C + C= C + …

H H H H H H H H
phenylthene+ phenylthene + phenylthene + …
(ii)the double bond joining the chloroethene molecule
break to free radicals
H C6H5 H C6H5 H C6H5 H C6H5

• C - C • + • C - C • + • C - C • + • C - C• + …

H H H H H H H H
Free phenylethene radical …[email protected] 292
 H C6H5 H C6H5 H C6H5 H C6H5 extension
of
-C-C - C -C - C -C - C -C– molecule/
polymer
H H H H H H H H
Since the molecule is a repetition of one
monomer, then the polymer is:
H H

(C–C ) n

H C6H5
[email protected] 293
Examples
Polyphenylthene has a molar mass of 4760.Calculate
the number of phenylethene molecules in the
polymer(C=12.0, H=1.0, )
Number of monomers/repeating units in monomer =
Molar mass polymer
Molar mass monomer
Þ Molar mass ethene (C8H8 )= 104
Þ Molar mass polyethene = 4760
Substituting 4760 = 45.7692 => 45 (whole number)
104
The commercial name of polyphenylethene is
polystyrene.
It is a very light durable plastic. [email protected] 294
Polystyrene is used:
(i)in making packaging material for delicate items like
computers, radios,calculators.
(ii)ceiling tiles
(iii)clothe linings

4.Formation of Polypropene
Polypropene is an addition polymer formed when
propene molecule/monomer join together to form a large
molecule/polymer at high temperatures and pressure.
During polymerization:
(i)many molecules are brought nearer to each other by
the high pressure(which reduces the volume occupied by
reacting particles) [email protected] 295
 H CH3 H CH3 H CH3 H CH3

C=C + C=C + C=C + C= C + …

H H H H H H H H
propene+ propene + propene + …
(ii)the double bond joining the chloroethene molecule
break to free radicals
H CH3 H CH3 H CH3 H CH3

• C - C • + • C - C • + • C - C • + • C - C• + …

H H H H H H H H
Free propene radical … [email protected] 296
 H CH3 H CH3 H CH3 H CH3 extension
of
-C-C - C -C - C -C - C -C– molecule/
polymer
H H H H H H H H
Since the molecule is a repetition of one
monomer, then the polymer is:
H H

(C–C ) n

H CH3
[email protected] 297
Polypropene has a molar mass of 4760.Calculate the
number of propene molecules in the polymer(C=12.0,
H=1.0, )
Number of monomers/repeating units in monomer =
Molar mass polymer
Molar mass monomer
Molar mass propene (C3H8 )= 44
Molar mass polyethene = 4760
Substituting 4760 = 108.1818 =>108 (whole number)
44
The commercial name of polypropene is polyproprene.
It is a very light durable plastic.

[email protected] 298
Polyproprene is used:
(i)in making packaging material for carrying
delicate items like computers, radios,,calculators.
(ii)clothe linings

5.Formation of Polytetrafluorothene
Polytetrafluorothene is an addition polymer formed when
tetrafluoroethene molecule/monomer join together to
form a large molecule/polymer at high temperatures and
pressure.
During polymerization:
(i)many molecules are brought nearer to each other by
the high pressure(which reduces the volume occupied by
reacting particles) [email protected] 299
 F F F F F F F F

C=C + C=C + C=C + C= C + …

F F F F F F F F
tetrafluoroethene+ tetrafluoroethene + …
(ii)the double bond joining the tetrafluoroethene
molecule break to free radicals
F F F F F F F F

• C - C • + • C - C • + • C - C • + • C - C• + …

F F F F F F F F
Free tetrafluoroethene radical …
[email protected] 300
 F F F F F F F F extension
of
-C-C - C -C - C -C - C -C– molecule/
polymer
F F F F F F F F
Since the molecule is a repetition of one
monomer, then the polymer is:
F F

(C–C ) n

F F
[email protected] 301
Examples
Polytetrafluorothene has a molar mass of 4760.
Calculate the number of tetrafluoroethene molecules
in the polymer(C=12.0, ,F=19 )
Number of monomers/repeating units in monomer =
Molar mass polymer
Molar mass monomer
Þ Molar mass ethene (C2F4 )= 62.5
Þ Molar mass polyethene = 4760
Substituting 4760 = 77.16 => 77 whole number
62.5

[email protected] 302
The commercial name of polytetrafluorethene(P.T.F.E)
is Teflon / P.T.F.E. It is a tough, non-transparent and
durable plastic.
P.T.F.E is used:
(i)in making plastic rope
(ii)water pipes
(iii)crates and boxes
5.Formation of rubber from Latex
Natural rubber is obtained from rubber trees.
During harvesting an incision is made on the rubber tree
to produce a milky white substance called latex.
Latex is a mixture of rubber and lots of water.
The latex is then added an acid to coagulate the rubber.
Natural rubber is a polymer of 2-methylbut-1,3-diene ;
[email protected] 303
 H CH3 H H

H - C = C – C = C - H

CH2=C (CH3) CH = CH2

During natural polymerization to rubber, one double C=C
bond break to self add to another molecule.
The double bond remaining move to carbon “2” thus;
H CH3 H H H CH3 H H

- C - C = C - C - C - C = C - C -

H H H H
[email protected] 304
Generally the structure of rubber is thus;

H CH3 H H

(- C - C = C - C -)n

H H
Pure rubber is soft and sticky.
It is used to make erasers, car tyres.
Most of it is vulcanized.
Vulcanization is the process of heating rubber with sulphur to make
it harder/tougher.
During vulcanization the sulphur atoms form a cross link between
chains of rubber molecules/polymers.
This decreases the number of C=C double bonds in the polymer. 305
[email protected]
 H CH3 H H H CH3 H H

- C - C - C - C - C - C - C - C -

H S H S H

H CH3 S H H CH3 S H

- C - C - C - C - C - C - C - C -

H H H H H H

Vulcanized rubber is used to make tyres, shoes and

valves. [email protected] 306
6.Formation of synthetic rubber
Synthetic rubber is able to resist action of oil, abrasion
and organic solvents which rubber cannot.
Common synthetic rubber is a polymer of 2-chlorobut-
1,3-diene ;

H Cl H H

CH2=C (Cl CH = CH2 //H - C = C – C = C - H

During polymerization to synthetic rubber, one double
C=C bond is broken to self add to another molecule.
The double bond remaining move to carbon “2” thus;

[email protected] 307
 H Cl H H H Cl H H

- C - C = C - C - C - C = C - C -

H H H H

Generally the structure of synthetic rubber is thus;

H Cl H H

-(- C - C = C - C -)n-

H H
Rubber is thus strengthened through vulcanization and
manufacture of synthetic rubber.
[email protected] 308
 (b)Condensation polymerization
Condensation polymerization is where two or more
small monomers join together to form a larger molecule
by elimination of a simple molecule. (usually water).
Condensation polymers acquire a different name from
the monomers as the two monomers are two different
compounds
During condensation polymerization:
(i)the two monomers are brought together by high
pressure to reduce distance between them.
(ii)monomers realign themselves at the functional
group.
(iii)from each functional group an element is removed
so as to form simple molecule (of usually H2O/HCl)
(iv)the two monomers join without the simple
[email protected] 309

molecule
 Examples of condensation polymerization
1.Formation of Nylon-6,6
Method 1: Nylon-6,6 can be made from the condensation
polymerization of hexan-1,6-dioic acid with hexan-1,6-diamine.
Amines are a group of homologous series with a general
formula R-NH2 and thus -NH2 as the functional group.
During the formation of Nylon-6,6:
(i)the two monomers are brought together by high pressure to
reduce distance between them and realign themselves at the
functional groups.

O O H H

H- O - C – (CH2 ) 4 – C – O - H + H –N – (CH2) 6 – N – H
[email protected] 310
 (iii)from each functional group an element is removed so as to
form a molecule of H2O and the two monomers join at the linkage

O O H H

H- O - C – (CH2 ) 4 – C – N – (CH2) 6 – N – H + H 2O
.
Polymer bond linkage
Nylon-6,6 derive its name from the two monomers each with
six carbon chain
Method 2: Nylon-6,6 can be made from the condensation
polymerization of hexan-1,6-dioyl dichloride with hexan-1,6-
diamine.
Hexan-1,6-dioyl dichloride belong to a group of homologous
series with a general formula R-OCl and -OCl as the functional
group.
The R-OCl is formed when the “OH” in R-OOH/alkanoic
[email protected] acid311
is replaced by Cl /chlorine/ Halogen
During the formation of Nylon-6,6:
(i)the two monomers are brought together by high
pressure to reduce distance between them and realign
themselves at the functional groups.

O O H H

Cl - C – (CH2 ) 4 – C – Cl + H –N – (CH2) 6 – N – H

(iii)from each functional group an element is removed so

as to form a molecule of HCl and the two monomers
join at the linkage .

[email protected] 312
 O O H H

Cl - C – (CH2 ) 4 – C –N – (CH2) 6 – N – H + HCl

Polymer bond linkage
The two monomers each has six carbon chain hence the
name “nylon-6,6”
The commercial name of Nylon-6,6 is Nylon It is a a
tough, elastic and durable plastic.
It is used to make clothes, plastic ropes and carpets.
2.Formation of Terylene
Method 1: Terylene can be made from the condensation
polymerization of ethan-1,2-diol with benzene-1,4-
dicarboxylic acid. [email protected] 313
Benzene-1,4-dicarboxylic acid is a group of homologous
series with a general formula R-COOH where R is a ring
of six carbon atom called Benzene ring .
The functional group is -COOH.
During the formation of Terylene:
(i)the two monomers are brought together by high
pressure to reduce distance between them and realign
themselves at the functional groups.
O O

H- O - C – C6H5 – C – O - H + H –O –CH2 CH2– O – H

(iii)from each functional group an element is removed so
as to form a molecule of H2O and the two monomers
join at the linkage . [email protected] 314
 O O

H- O - C – C6H5 – C – O –CH2 CH2– O – H + H2O

Polymer bond linkage of terylene
Method 2: Terylene can be made from the condensation
polymerization of benzene-1,4-dioyl dichloride with ethan-1,2-
diol.
Benzene-1,4-dioyl dichloride belong to a group of homologous
series with a general formula R-OCl and thus -OCl as the
functional group and R as a benzene ring.
The R-OCl is formed when the “OH” in R-OOH is replaced by
Cl/chlorine/Halogen
During the formation of Terylene
(i)the two monomers are brought together by high pressure to
reduce distance between them and realign themselves at the
[email protected] 315
functional groups.
 O O

Cl -C – C6H5 – C – Cl +H –O –CH2 CH2– O – H

(iii)from each functional group an element is removed so

as to form a molecule of HCl and the two monomers
join at the linkage .
O O

Cl - C – C6H5 – C –O –CH2 CH2– O – H + HCl

Polymer bond linkage of terylene
The commercial name of terylene is Polyester /polyster It
is a a tough, elastic and durable plastic. It is used to make
clothes, plastic ropes and sails and plastic model kits.
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institution to be a user
consumer of pirated soft wares.
Legal action can easily be taken
against both you and the
institution at your cost!!!
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 THE END
EVANS O. OMATO
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Dedicated to all Chemistry students IN
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